Water → HCID 123578460, compound

HRID 1508648Notes

Reaction equation

HRID 1508648 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([CH:12]([CH2:16][CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH:13]([OH:15])[CH3:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.O>C(OCC)(=O)C>[CH3:1][S:2]([O:15][CH:13]([CH:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:16][CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:20]([CH3:21])[CH3:22])[CH:23]([CH3:25])[CH3:24])[CH3:14])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 123667565HCID 123667565, compound

Product 1

HCID 123578460HCID 123578460, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

0.46 mL of methanesulfonyl chloride was added dropwise to a solution of 1.0 g of 3-phenyl-5-((tris(propan-2-yl)silyl)oxy)pentan-2-ol and 1.67 mL of triethylamine in 10 mL of an ethyl acetate at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 5.5 hours. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated, and it was washed with a saturated sodium chloride aqueous solution and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, so as to obtain 1.2 g of 3-phenyl-5-((tris(propan-2-yl)silyl)oxy)pentan-2-yl methanesulfonate in the form of a yellow oily product.

Workup

  1. washit was washed with a saturated sodium chloride aqueous solution
  2. dry with materialwas then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-68364e268dd24c02a07462c8a7708a25
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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