Dimethylformamide → HCID 20077568, compound

Participants

Reaction Conditions

Reaction Steps

A solution of compound Q (40 g) in ether (100 ml) was added dropwise to a solution of n-butyllithium (1.6M solution in hexane, 138 ml) in ether (300 ml) at -70° C. under an atmosphere of argon. The mixture was stirred for 1 hour at this temperature and then N,N-dimethylformamide (30 ml) was added dropwise. The mixture was stirred for 30 minutes at -70° C., then warmed to -40° C. Excess saturated aqueous ammonium chloride solution was added and the mixture allowed to warm to ambient temperature. The layers were separated and the aqueous phase extracted three times with ether. The organic phases were combined, dried (MgSO4), and concentrated. The residue was purified by column chromatography, eluting with 25% ethyl acetate/hexane (v/v), to give 2-tert-butyldimethylsilylthiazole-5-carboxaldehyde (R) (31 g, 69% yield) as an oil; NMR: 0.32(6H,s), 0.89(9H,s), 8.55(1H,s), 10.0(1H,s).

Provenance & Evidence