Water → 3-(5-Methyltetrazol-1-yl)-5-(trifluoromethyl)phenylmethanol

Methyl 3-(5-methyltetrazol-1-yl)-5-(trifluoromethyl)benzoate (1.56 g, 5.5 mmol) was dissolved in ether (20 ml) and cooled in ice. Water (98 ml, 98 mg, 5.5 mmol) then lithium borohydride (131 mg, 6 mmol) were added and the mixture was stirred at room temperature for 1 hour. Tetrahydrofuran (10 ml) was added and the mixture was stirred at room temperature for 1 hour. Methanol (5 ml) was added and the solvent was evaporated under reduced pressure. Saturated aqueous sodium hydrogen carbonate (20 ml) and water (10 ml) were added and the mixture was extracted with dichloromethane (10×10 ml). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by MPLC on silica gel, eluting with ethyl acetatelhexane (50:50 increasing to 100:0) to give 3-(5-methyltetrazol-1-yl)-5-(trifluoromethyl)phenylmethanol as a colorless oil (1.00 g, 70%), 1H (CDCl 3) δ 7.84 (1H, s), 7.75 (1H, s), 7.67 (1H, s), 4.92 (2H, s), 2.67 (3H, s), and 1.86 (1H, br s). m/z 259 (M+H+).

1. temperaturecooled in ice
2. stirringthe mixture was stirred at room temperature for 1 hour
3. customthe solvent was evaporated under reduced pressure
4. additionSaturated aqueous sodium hydrogen carbonate (20 ml) and water (10 ml) were added
5. extractionthe mixture was extracted with dichloromethane (10×10 ml)
6. dry with materialThe combined organic fractions were dried (MgSO4)
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by MPLC on silica gel
9. washeluting with ethyl acetatelhexane (50:50 increasing to 100:0)

ORD record

ord-866eec70f3d64c08874778303b11d289

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05830892