Sodium borohydride → HCID 20190714, compound

Participants

Reaction Steps

The crude anil (IV) (7.2 g.) was dissolved in MeOH (100 ml.), cooled in an ice bath and then NaBH4 (3.6 g.) added portionwise. The mixture was refluxed for 1 hr. and cooled. The solvent was removed and the residue treated with EtOAc/H2O. The EtOAc extracts were combined, dried over MgSO4 and solvent removed in vacuo. Yield, 6.7 g. The TLC showed two spots (most likely two isomers). The mixture was run through a HPLC using EtOAc/acetone (5:1). The mixture was not easily separated and the main portion (4 g.) was still a mixture. The mixture was carried through the rest of the synthesis. Also obtained was the fast component pure (0.7 g.) and the slow component pure (0.4 g.)

Provenance & Evidence