4-Bromobenzaldehyde → HCID 86725944, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of CuI (5.67 g, 29.88 mmol) in tetrahydrofuran (70 mL) was added phenyl lithium (1.8M dibutyl ether) (33.2 mL, 59.76 mmol) at −78° C. and the resulting mixture was allowed to stir at −30° C. for 2 h. To the resulting reaction mixture at −78° c. was added the pre-cooled solution of cyano-(1,4-dioxa-spiro[4.5]dec-8-ylidene)-acetic acid ethyl ester (262) in tetrahydrofuran (30 mL) and the resulting mixture was allowed to stir at −30° C. for 1 h. The reaction was monitored by silica TLC (P-anisaldehyde active). The reaction mixture was quenched with saturated NH4Cl-solution and the reaction mixture was diluted with ethyl acetate and the organic layer was separated. The organic part was dried over Na2SO4 and concentrated under reduced pressure, The resulting crude product was purified over silica gel (normal, 100-200 mesh) column chromatography using a gradient eluent 2% to 10% ethyl acetate in hexane to get cyano-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-acetic acid ethyl ester (263) (3.8 g, 57.91%), as colorless gummy liquid.

Provenance & Evidence