Methanesulfonyl chloride → (1-Phenylcyclopentyl)methyl methanesulfonate

HRID 1409553

반응식

HRID 1409553 반응식
[C:1]1([C:7]2([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[C:1]1([C:7]2([CH2:12][O:13][S:15]([CH3:14])(=[O:17])=[O:16])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 123544(1-Phenylcyclopentyl)methanol

생성물 1

HCID 19437914(1-Phenylcyclopentyl)methyl methanesulfonate수율 61.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (1-phenyl-cyclopentyl)-methanol (11.5 g, 64.34 mmol) in DCM (100 ml) was added TEA (17.5 ml, 130.68 mmol) and followed by methanesulfonyl chloride (MsCl) (8.9 g, 78.4 mmol) was added drop wise at 0° C. and the reaction mixture was stirred at RT for 16 h. After completion of the reaction, it was quenched with water and concentrated. Then the crude product was dissolved in DCM, extracted with DCM and the organic layer was washed with water, and brine and then dried over Na2SO4. The combined organic layer was concentrated to get crude methanesulfonic acid 1-phenyl-cyclopentylmethyl ester (10 g, crude) as a white solid.

후처리

  1. additionwas added drop wise at 0° C.
  2. customAfter completion of the reaction, it
  3. customwas quenched with water
  4. concentrationconcentrated
  5. dissolutionThen the crude product was dissolved in DCM
  6. extractionextracted with DCM
  7. washthe organic layer was washed with water, and brine
  8. dry with materialdried over Na2SO4
  9. concentrationThe combined organic layer was concentrated

출처 및 근거

ORD 기록
ord-087fa2896d7a4b46841ac6d5ff349e6f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921388B2

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