Formaldehyde → HCID 10138875, compound

Participants

Reaction Steps

A solution of 114 (2.72 g, 6.43 mmol), formaldehyde (12.3M, 2.62 mL, 32.2 mmol), sodium cyanoborohydride (1.0M in tetrahydrofuran, 32.2 mL, 32.2 mmol), and methanol (100 mL) were heated at reflux for 1 h. The contents of the reaction flask were cooled and the solvent was removed in vacuo. Sat. sodium bicarbonate was added and the resulting mixture was extracted with ethyl acetate (3×). The combined organic extracts were dried with magnesium sulfate (anh.) and filtered. The filtrate was removed by rotary evaporation to give a colorless oil. Trituration with hexane:ether (1:1) gave 115 as a white solid (2.21 g, 4.90 mmol, 76.2%).

Provenance & Evidence