Dimethylformamide → HCID 89479126, compound

Participants

Reaction Conditions

Reaction Steps

5 g of the compound [1-1] was dissolved in 100 mL of tetrahydrofuran and cooled to −78° C. Thereafter, 31.2 mL of n-butyllithium (1.6 M hexane solution) was added thereto, and the mixture was stirred for 1 hour at the same temperature. 774 μL of N, N-dimethylformamide was added to the produced white suspension, which was stirred for 5 hours while gradually heating back to room temperature. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-50/50), to obtain 514 mg of tert-butyl[(1S)-1-(4-formylphenyl) ethyl]carbamate [15-1] (hereinafter, referred to as the compound [15-1]) as a pale yellow amorphous.

Provenance & Evidence