Methanesulfonyl chloride → HCID 18790451, compound

HRID 1940109Notes

Reaction equation

HRID 1940109 reaction equation
C([C:5](=[C:20]([CH2:24][CH2:25][OH:26])[CH2:21][CH2:22][OH:23])[O:6][SiH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(C)(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>CCOCC>[CH3:27][S:28]([O:26][CH2:25][CH2:24][C:20](=[CH:5][O:6][Si:7]([C:20]([CH3:24])([CH3:21])[CH3:5])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:21][CH2:22][O:23][S:28]([CH3:27])(=[O:30])=[O:29])(=[O:30])=[O:29]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1317195333-(Tertbutyldiphenylsilyloxymethylene)-pentane-1,5-diol

Product 1

HCID 18790451HCID 18790451, compoundYield 169.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. ether (300 mL) solution of 3-(tertbutyldiphenylsilyloxymethylene)-pentane-1,5-diol (6.9 g, 19 mmol) was added methanesulfonyl chloride (4.3 mL, 56 mmol) followed by Et3 N (7.7 mL, 56 mmol). After 3-16 hours, gradually warming to ambient temperature, the reaction was washed with water, brine, dried over MgSO4, and concentrated to give the 1,5-bis(methanesulfonyloxy)-3-(tert-butyldiphenylsilyloxymethylene)-pentane 8.5 g (90%) as a colorless oil that was used without further purification.

Workup

  1. washthe reaction was washed with water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-855afa69df6a4683bf82c25df9653dd7
Source dataset
uspto-grants-1997_12
Patent number
US05698578

Reaction notes

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