Sodium borohydride → HCID 57419668, compound

Temperature

45 °C

The allyl ether from stage (ii) (800 mg, 4.16 mmol) was dissolved in THF (10 mL) and treated with palladium tetrakis(triphenylphosphine) (481 mg, 0.42 mmol) followed by sodium borohydride (944 mg, 25 mmol). The mixture was then heated to 45° C. and stirred at this temperature for 15 h. After cooling to room temperature the THF was evaporated and the residue partitioned between 2M NaOH solution (25 mL) and diethyl ether (25 mL). The aqueous layer was separated and the organic layer re-extracted with 2M NaOH solution (25 mL). The combined aqueous layers were neutralised to pH 7–8 with concentrated hydrochloric acid and extracted with EtOAc (2×25 mL). The combined organic extracts were dried (MgSO4) and evaporated to a clear oil of the title phenol which solidified upon standing (540 mg, 85%); 4.14 (2H, s), 4.17 (2H, s), 6.63–6.68 (2H, m), 7.04 (1H, d)

1. customwas evaporated
2. customthe residue partitioned between 2M NaOH solution (25 mL) and diethyl ether (25 mL)
3. customThe aqueous layer was separated
4. extractionthe organic layer re-extracted with 2M NaOH solution (25 mL)
5. extractionextracted with EtOAc (2×25 mL)
6. dry with materialThe combined organic extracts were dried (MgSO4)
7. customevaporated to a clear oil of the title phenol which

ORD record

ord-7af69bb09f9d4269a6e2273d2783ddb6

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129234B2