Water → HCID 131725687, compound

Participants

Reaction Steps

o-Chlorobenzaldehyde (2.0 g, 1.62 ml, 14.23 mmol) was added via syringe to an agitated mixture of potassium cyanide (2.793 g, 43.8 mmol) and a vanadium catalyst* of Formula (7) (90 mg, 14.23×10−2 mmol) in CH2Cl2 (55 ml), followed by 2,6-lutidine (0.147 g, 0.16 ml, 1.37 mmol) and water (0.25 g, 0.25 ml, 13.66 mmol). The slurry was cooled to a temperature of −6° C. and acetic anhydride (3.08 g, 2.85 ml, 30.17 mmol) was added via a syringe. The slurry was agitated at a temperature of −5° C. to 0° C. Analysis by G.C. showed that the reaction had gone to 51% conversion (62% e.e.) after 4 hrs and to 61% conversion (53% e.e.) after 7 hrs. The excess potassium cyanide was filtered off and the product was washed with dichloromethane before the filtrates were reduced in vacuo. The residues were dissolved in 10:2 v/v hexane:ethyl acetate and the catalyst was removed by passing the mixture through a bed of silica and washing with 10:1 v/v hexane:ethyl acetate.

Provenance & Evidence