Benzyl Alcohol → 2-Benzyloxy-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxyethane

HRID 990094Notes

Reaction equation

HRID 990094 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[CH:6]1[O:8][CH2:7]1.[CH2:18]([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[H-].[Na+]>O1CCCC1>[CH2:18]([O:25][CH2:7][CH:6]([C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:11]=[C:10]([C:12]([F:14])([F:13])[F:15])[CH:9]=1)[OH:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydride2×HCID 139032682-[3,5-Bis(trifluoromethyl)phenyl]oxirane

Product 1

HCID 184196782-Benzyloxy-1-(3,5-bis(trifluoromethyl)phenyl)-1-hydroxyethane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 3,5-bis(trifluoromethyl)styrene oxide (Description 12, 0.5 g) and benzyl alcohol (1 g) in tetrahydrofuran (10 ml) was added sodium hydride (50% in mineral oil, 48 mg). The solution was stirred at room temperature for 16 hours. A further addition of sodium hydride (20 mg) was made and the solution heated to reflux for 2 hours. The cooled solution was evaporated to dryness and the residue purified by chromatography on silica (eluting with increasing concentrations of ethyl acetate in isohexane 0-20%) to provide the title compound. 1H NMR (360 MHz, CDCl3) δ 3.22 (1H, d J 3.1 Hz), 3.48 (1H, dd J 8.2 Hz and 9.6 Hz), 3.67 (1H, dd J 9.7 Hz and 3.5 Hz), 4.57 (1H, s), 4.98 (1H, m), 7.23-7.37 (5H, m), 7.80 (1H, s), 7.83 (2H, s).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 2 hours
  3. customThe cooled solution was evaporated to dryness
  4. customthe residue purified by chromatography on silica (eluting with increasing concentrations of ethyl acetate in isohexane 0-20%)

Sources & evidence

ORD record
ord-cf52f95bdc5846959e2d29e88616bef5
Source dataset
uspto-grants-2002_10
Patent number
US06458830B1

Reaction notes

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