Ammonium Chloride → HCID 67995940, compound

Participants

Reaction Steps

Allylmagnesium chloride (2 mol/L in tetrahydrofuran, 56 ml) is added to a solution of cyano-(3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-ylidene)-acetic acid ethyl ester (13.7 g) and CuI (2.7 g) in tetrahydrofuran (100 mL) under argon atmosphere and chilled in an ice bath. The mixture is warmed in the cooling bath to room temperature and stirred overnight. Aqueous NH4Cl solution is then added and the resulting mixture is extracted with tert-butyl methyl ether. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:02:3) to give the title compound. Yield: 5.0 g (31% of theory); Mass spectrum (ESI+): m/z=336 [M+H]+.

Provenance & Evidence