Methyl iodide → (2-(Cyclopentyl(methoxy)methyl)-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilane

HRID 2075033Notes

Reaction equation

HRID 2075033 reaction equation
[Si:1]([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[CH:20]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[OH:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:29]I>C1COCC1>[CH:22]1([CH:20]([O:21][CH3:29])[C:11]2[CH:12]=[CH:13][C:14]([C:16]([F:18])([F:19])[F:17])=[CH:15][C:10]=2[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58968632(2-((Tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)-phenyl)-(cyclopentyl)methanol

Product 1

HCID 58968676(2-(Cyclopentyl(methoxy)methyl)-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilaneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)-phenyl)-(cyclopentyl)-methanol (126.8 mg, 0.33 mmol) in THF at 0° C. was added sodium hydride (39.2 mg, 0.98 mmol). The mixture was stirred at room temperature for 30 minutes, cooled to 0° C. and methyl iodide (100 μL, 1.6 mmol) was added. The mixture was stirred at room temperature overnight. Solvent was removed and the residue was purified by chromatography over 12+S Biotage silica column (eluted with 0-20% ethyl acetate in hexanes) to afford the title compound as a colorless oil (120 mg, 91%). 1H NMR (400 MHz, CDCl3) δ ppm 0.13 (s, 6H) 0.96 (s, 9H) 1.11-1.21 (m, 1H) 1.30-1.40 (m, 1H) 1.44-1.70 (m, 5H) 1.77-1.86 (m, 1H) 2.13-2.23 (m, 1H) 3.15 (s, 3H) 4.20 (d, J=7.88 Hz, 1H) 4.77 (d, J=13.69 Hz, 1H) 4.89 (d, J=13.28 Hz, 1H) 7.46-7.55 (m, 2H) 7.77 (s, 1H).

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe mixture was stirred at room temperature overnight
  3. customSolvent was removed
  4. customthe residue was purified by chromatography over 12+S Biotage silica column (eluted with 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ced4363837164e0ca9858fe1ecd280c1
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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