Sodium borohydride → HCID 21904669, compound

Participants

Reaction Conditions

Reaction Steps

The allyl ether from stage (i) (1.40 g, 6.3 mmol) was dissolved in THF (63 mL) and treated with sodium borohydride (1.19 g, 31.5 mmol) followed by palladium tetrakis(triphenylphosphine) (730 mg, 0.63 mmol), and the mixture was heated to 40° C. overnight. After cooling to room temperature 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 re-extracted with 2M NaOH (25 mL). The combined aqueous layers were acidified with concentrated hydrochloric acid to pH 7–8 and extracted with EtOAc (2×25 mL). The combined organic extracts were dried (MgSO4) and evaporated to a brown oil (10.73 g, 93%) of the desired title phenol; δH (CDCl3, 400 MHz) 2.17 (3H, s), 3.07 (2H, m), 4.33 (2H, m), 6.20 (1H, s), 6.31 (1H, s); MS m/z (TS+) 183 (MH+).

Provenance & Evidence