Tributylstannane → HCID 11733611, compound

Participants

Reaction Steps

To dry tetrahydrofuran (80 mL) cooled to −78° C. was added a solution of lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 18.36 mL, 37.5 mmol) followed by tri-n-butyltin hydride (9.81 mL, 37.5 mmol) dropwise. After 5 minutes, the mixture was placed in an ice water bath for 0.5 hours, then recooled to −78° C. 4-Methoxybenzaldehyde (4.45 mL, 37.5 mmol) was added dropwise, and the reaction mixture was stirred at this temperature for 1.5 hours. Afterwards, methyl chloroformate (3.41 mL, 44.1 mmol) was added dropwise, the cooling bath was removed, and the mixture was allowed to stir overnight at room temperature. Then a solution of saturated aqueous ammonium chloride (100 mL) was added followed by extraction with ethyl acetate. The organic extract was dried, filtered and concentrated. The residue was purified by chromatography (silica gel, ethyl acetate in hexanes) which afforded 6.7 g, (38%) of the title compound.

Provenance & Evidence