Formaldehyde → HCID 69586068, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of diisopropylamine (160 μL, 1.14 mmol) under argon at −5° C. in THF (3 mL) was added n-butyllithium solution (0.43 mL, 2.5 M in hexanes, 1.08 mmol). After 15 min, the reaction mixture was cooled to −78° C. and a solution of Example 5 Part E compound (209 mg, 0.5 mmol) in THF (1 mL) was then added over 2 min. After an additional 15 min, DMPU was added (2 mL) and the solution warmed to 0° C. Formaldehyde gas (by the pyrolysis of paraformaldehyde [300 mg, 10 mmol] at 190° C.) was introduced to the reaction mixture by a gas inlet tube. The reaction mixture was stirred for 1 h, diluted with EtOAc, washed once with 5% potassium hydrogen sulfate, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel (1:39:360 HOAc/MeOH/CH2Cl2 as elutent) provided the title compound as a white solid, 136 mg (61% yield). LC/MS gave the correct molecular ion [(M+H)+=447] for the desired compound.

Provenance & Evidence