Methanesulfonyl chloride → 2-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethyl methanesulfonate

HRID 916825Notes

Reaction equation

HRID 916825 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:27][S:28]([O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:10][CH:11]=1)(=[O:30])=[O:29]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 112882212-(4-((Tert-butyldimethylsilyl)oxy)phenyl)ethan-1-ol

Product 1

HCID 597681012-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(4-((tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol (653 mg) and diisopropylethylamine (1.8 ml) in DCM (15 ml) at 0° under nitrogen was treated with methanesulfonyl chloride (0.44 ml) and the mixture was stirred at 0° C. for 6 h. Saturated NaHCO3 solution was added and the mixture stirred for 15 min. Water (20 ml) was added and the mixture was extracted with DCM. The extract was dried (Na2SO4) and the solvent evaporated in vacuo to give the title compound (904 mg). LCMS RT=3.85 min.

Workup

  1. stirringthe mixture stirred for 15 min
  2. extractionthe mixture was extracted with DCM
  3. dry with materialThe extract was dried (Na2SO4)
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-3360c2922bbf45d4bb8785bd341ef57c
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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