Methyl 2-formylbenzoate → HCID 14748254, compound

Participants

Reaction Conditions

Reaction Steps

To 351 mg (1.48 mmol) of trans-3,4-dihydro-2,2-dimethyl-3-hydroxy-7-nitro-2H-1-benzopyran-4-amine in methanol (3 mL) containing 290 mg (1.77 mmol) of 2-carbomethoxybenzaldehyde was added 1.5 mL (0.75 mmol) of 0.5M zinc chloride-modified sodium cyanoborohydride in methanol, prepared according to the method of Kim et al. J. Org. Chem. 50 (11), 1927 (1985). After stirring at 50° C. for two days, the reaction mixture was quenched with saturated NaHCO3 solution, extracted into CH2Cl2, dried (K2CO3) and concentrated. The residue was dissolved in a minimal amount of THF and silica gel was added. The solvent was removed in vacuo and the silica gel was applied onto the head of a flash column. Eluting with 20%→50% ether/CH2Cl2 gave 390 mg of the title compound as a pale yellow powder, m.p. 249°-250° C.

Provenance & Evidence