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May 12, 2009
14:22
Double C-alkylation
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To a suspension of NaH (17.6 g, 60%) in DMF (150 mL) at ice-bath temperature with mechanical stirring was added over a one hour period a mixture of 4-chlorobenzyl cyanide (30.3 g) and 1,3-dibromopropane (22.3 mL, 44.5 g). The reaction mixture was stirred for an additional 1 hour, and isopropyl alcohol (10 mL) was added [...]
September 30, 2008
11:48
Selective cleavage of Arylacetates to Phenols
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Morpholine (1.1 mL, 0.012 mol) was added to a solution of ethyl 4-(6-acetoxy-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)butanoate in 10 mL THF and the resulting mixture was refluxed for 1 h. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was evaporated, diluted with ethyl acetate, washed with water, dried over sodium sulfate and [...]
September 25, 2008
0:24
Baeyer-Villager Oxidation
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To a mixture of 4-(6-acetyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)butanoate (1.3 g, 0.003 mol), urea hydrogen peroxide (0.85 g, 0.009 mol) and sodium bicarbonate (0.76 g, 0.009 mol) in anhydrous dichloromethane (10 mL) under nitrogen atmosphere at ice-bath temperature was added trifluoroacetic anhydride (0.8 mL, 0.006 mol) drop-wise over a period of 10 minutes. The reaction mixture was gradually warmed to room [...]
September 12, 2008
19:20
DIBAL Reduction of Ester to Alcohol
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(E)-Ethyl 3-(2-chlorophenyl)acrylate (1.5 g, 0.007 mol) was dissolved in 15 mL of anhydrous dichloromethane, cooled to -78 oC and treated with a solution of di-iso-butylaluminum hydride (1.0 M solution in hexane, 21.4 mL, 0.021 mol) over a period of 20 minutes (the solution turned yellow in color). After 1.5 hours total at -78 oC, the [...]
August 22, 2008
11:00
Selective O-demethylation
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A mixture of 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (3.4 g, 0.009 mol), sodium ethanethiolate (3.8 g, 0.045 mol) in 34 mL DMF was heated at 50 oC for overnight (12 h). The reaction mixture was cooled to rt and diluted with water (100 mL) and ethyl acetate (100 mL). The unreacted starting material was separated by extracting into the [...]
August 20, 2008
20:19
Bromination
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A mixture of 1-phenylethanol (1.21 mL) and 48% HBr in water (12 mL) was stirred at room temperature for overnight (12 h). The reaction mixture was diluted with 50 mL ethyl acetate, washed with 50 mL aqueous saturated NaHCO3 solution, dried over Na2SO4 and evaporated under reduced pressure to give (1-bromoethyl)benzene as a light brown oil [...]
July 12, 2008
23:11
C-Alkylation
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A 1.6 M solution of n-butyllithium in hexane (9.36 mL) was added to a stirred solution of diisopropylamine (2.22 mL) in THF (15 mL) at -5 to 0 oC. After being stirred at -5 to 0 oC for 30 min, the reaction mixture was cooled to -78 oC and ethyl isobutyrate (1.9 mL) was added. [...]
June 07, 2008
16:06
Phenol
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To a suspension of compound containing an acetyl (-COCH3) group (0.01 mol) in 50 mL of dichloromethane was added m-chloroperbenzoic acid (0.03 mL) in three small portions at room temperature. The resulting mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with 50 mL dichloromethane and washed successively with 2% [...]
May 19, 2008
0:37
Dialkyl ether
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To a suspension of sodium hydride (0.0004 mol) and alkyl methanesulfonate (0.0004 mol) in 5 mL THF at ice-bath temperature was added benzyl alcohol (0.0004 mol) in 5 mL THF dropwise. After the addition was complete, the resulting reaction mixture was allowed to warm to room temperature and then heated at 50 oC for 12 [...]
April 19, 2008
0:31
Chlorosulfonylation
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To chlorosulfonic acid (0.9 mol) at 0 oC was slowly added salicylic acid (0.09 mol) with constant stirring. After all the salicylic acid was dissolved, the mixture was heated at 75 oC for 1 h. The mixture was cooled to room temperature and then carefully added to 250 g of crushed ice. The white solid [...]

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