Water → HCID 58079381, compound

HRID 1616977Notes

Reaction equation

HRID 1616977 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS([Cl:28])(=O)=O.O>ClCCl>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][Cl:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10857542Benzenemethanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

Product 1

HCID 58079381HCID 58079381, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(tert-Butyldimethylsilyloxy)benzyl alcohol (101) (prepared by the process described in Wu, Y.-C. et al., J. Am. Chem. Soc., 130, 7148-7152 (2008)) (7.94 g, 31.4 mmol) was dissolved in dichloromethane (150 mL), and cooled to 0° C. To this were sequentially added triethylamine (9.10 mL, 66.7 mmol) and methanesulfonyl chloride (3.80 mL, 49.1 mmol) and stirred for 25 hours after warming up to room temperature. To this was added water, and the product was extracted with dichloromethane (×3). The organic layer was sequentially washed with water (×1) and saturated brine (×1), and dried over anhydrous sodium sulfate. After filtration, the mixture was concentrated under reduced pressure and the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate═95/1) to give 3-(tert-butyldimethylsilyloxy)benzyl chloride (102) as a colorless oily substance (5.90 g, 23.0 mmol, 73.1%).

Workup

  1. temperatureafter warming up to room temperature
  2. extractionthe product was extracted with dichloromethane (×3)
  3. washThe organic layer was sequentially washed with water (×1) and saturated brine (×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe mixture was concentrated under reduced pressure
  7. customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate═95/1)

Sources & evidence

ORD record
ord-4728e7b8583c49838d6dd9b3b2529d11
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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