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Synthesis of thioesters from tosylates using potassium acetate

J. Med. Chem, 1994, 37, 4118. Reagents: Alkyl tosylate : 1 equivalent Potassium thioacetate :2 eq or excess DMF : solvent Thioester product : > 70% expected yield Procedure: The alkyl tosylate is dissolved in N,N-dimethylforamide (2 mL/mmol) and is added dropwise to a stirred solution of potassium thioacetate (2 eq) in N,N-dimethylformamide (1... [Read More...]

Preparation of nitrotoluene from toluene and sulfuric acid and nitric acid

Reagents: Toluene : 1 equivalent Concentrated sulfuric acid : excess Nitric acid: excess Nitrotoluene : >80% expected yield Procedure: The aromatic toluene compound is dissolved in cold conc. sulfuric acid (2 mL/mmol) at 0 oC.  A solution of nitric acid (5 eq) in sulfuric acid (0.2-1; v-v) is added drop wise over time and stirred... [Read More...]

Preparation of acetate esters from alcohols and acetic anhydride

Reagents: Alcohol : 1 equivalent Acetic anhydride : 2 eq or excess Triethylamine : 2 eq or excess Dichloromethane : solvent Alkyl acetate : >90% expected yield Procedure: To a stirred solution of the alcohol (1 eq) and triethylamine (2 eq) in CH2Cl2 (1 mL/mmol of alcohol) in an ice-bath is added acetic anhydride (2 eq) drop wise.  A cloudy fume... [Read More...]

Synthesis of epoxides from aldehydes using trimethylsulfonium methyl sulfate

Reagents: Aldehyde : 1 equivalent Trimethylsulfonium methyl sulfate : 1.2 eq 50% aqueous NaOH : 0.5 mL/mmol of aldehyde Dichloromethane : solvent Epoxide :  70-90% expected yield Procedure: Trimethylsulfonium methyl sulfate (1.2 eq) and 50% aqueous NaOH (0.5 mL/mmol of aldehyde) are added to a solution of the aldehyde in CH2Cl2 (3 mL/mmol), and the... [Read More...]

Addition of azides to the alpha carbon of carbonyls using Trisyl azide and KHMDS

J. Org. Chem, 1994, 59, 2304. Reagents: Carbonyl : 1 equivalent Trisyl azide : 1.1 eq KHMDS : 1 eq Azide product : 60 – 80% expected yield Procedure: To a precooled (-78 oC) solution of KHMDS (1.3 eq) in toluene (0.5 M) in dry THF (3 mL/mmol KHMDS) is added (1 eq) of the carbonyl-oxazolidinone in dry THF (2 mL/mmol) via cannula, and the resulting... [Read More...]