Water → HCID 67402674, compound

HRID 1186335Notes

Reaction equation

HRID 1186335 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)[CH2:3][OH:4].C(N(CC)CC)C.[CH:22]([Si:25](Cl)([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].O>CN(C)C=O.C(OCC)(=O)C>[OH:1][CH:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=1)[CH2:3][O:4][Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 114811481-[4-(Trifluoromethyl)phenyl]ethane-1,2-diol

Product 1

HCID 67402674HCID 67402674, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1,2-Dihydroxyethyl)-4-(trifluoromethyl)benzene (81.0 mg, 0.393 mmol) and triethylamine (57.6 μL, 0.413 mmol) were dissolved in N,N-dimethylformamide (1.6 mL). To this, triisopropylsilyl chloride (87.2 μL, 0.413 mmol) was added under a nitrogen atmosphere at 0° C. and the mixture was stirred at room temperature for 2 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give 1-(1-hydroxy-2-triisopropylsiloxyethyl)-4-(trifluoromethyl)benzene (Compound CM) (117 mg, yield: 82%).

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-e8c0b778a5f8460d86a3469caca49f8e
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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