Sodium borohydride → HCID 21904667, compound

Participants

Reaction Conditions

Reaction Steps

The allyl ether from stage (i) (850 mg, 3.8 mmol) was dissolved in THF (38 mL) and treated with palladium tetrakis(triphenylphosphine) (440 mg, 0.38 mmol) and sodium borohydride (719 mg, 19 mmol). The reaction mixture was then heated to 45° C. for 18 h. After cooling to room temperature most of the THF was evaporated and the residue was partitioned between 2M NaOH (25 mL) and diethyl ether (25 mL). The aqueous layer was separated and the organic layer was re-extracted with 2M NaOH (25 mL). The combined aqueous layers were neutralised to pH 7–8 with concentrated HCl and extracted with EtOAc (2×25 mL). The combined organic extracts were dried (MgSO4) and evaporated to an orange solid of the title phenol (530 mg, 76%); δH (CDCl3, 400 MHz) 2.20 (3H, s), 2.41 (3H, s), 3.83 (3H, s), 6.26 (1H, s), 6.29 (1H, s); MS m/z (ES−) 183 (M−H+).

Provenance & Evidence