Tetrabutylammonium Fluoride → (S)-[2-(cyclohexyl-methoxy-methyl)-5-trifluoromethyl-phenyl]-methanol

HRID 2075025Notes

Reaction equation

HRID 2075025 reaction equation
C([Si]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1[C@H:20]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[O:21][CH3:22])(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:23]1([C@H:20]([O:21][CH3:22])[C:11]2[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][C:10]=2[CH2:9][OH:8])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58968729(S)-tert-butyl-[2-(cyclohexyl-methoxy-methyl)-5-trifluoromethyl-benzyloxy]-dimethyl-silane

Product 1

HCID 58968688(S)-[2-(cyclohexyl-methoxy-methyl)-5-trifluoromethyl-phenyl]-methanolYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl-[2-(cyclohexyl-methoxy-methyl)-5-trifluoromethyl-benzyloxy]-dimethyl-silane (1.13 g, 2.4 mmol) in THF (5 ml) was added a solution of tetrabutylammonium fluoride (4.8 ml, 1 M, 4.8 mmol) at room temperature and stirred for overnight. The reaction mixture was concentrated in vacuo and purified on Biotage column 25+M, eluting with 0-30% ethyl acetate in heptane (10 CV), 30% (2 CV) to yield the title compound (0.6 g, 73%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 0.8 m (m, 2H) 1.1 (m, 4H) 1.3 (m, 1H) 1.5 (m, 2H) 1.6 (m, 1H) 2.0 (d, J=12.9, 1H) 2.3 (m, 1H) 3.1 (s, 3H) 4.0 (d, J=7.9, 1H) 4.7 (dd, J=13.7 & 7.5 Hz, 2H) 7.3 (d, J=8.3 Hz, 1H) 7.4 (d, J=7.8 Hz, 1H) 7.7 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified on Biotage column 25+M
  3. washeluting with 0-30% ethyl acetate in heptane (10 CV), 30% (2 CV)

Sources & evidence

ORD record
ord-af2e70773c924db1bc888baa96038fc7
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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