Triethylamine → (S)-tetrahydrofuran-3-yl methanesulfonate

HRID 2280629노트

반응식

HRID 2280629 반응식
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>ClCCl>[CH3:14][S:15]([O:6][C@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:17])=[O:16]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

생성물 1

HCID 57561588(S)-tetrahydrofuran-3-yl methanesulfonate수율 92.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(S)-Tetrahydrofuran-3-ol 2a (300 mg, 3.40 mmol) and triethylamine (687 mg, 6.80 mmol) were dissolved in 20 mL of dichloromethane in an ice bath, followed by addition of methanesulfonyl chloride (908 mg, 7.93 mmol). The reaction solution was warmed up to room temperature and stirred for 2 hours. The resulting solution was mixed with 10 mL of dichloromethane, washed with water (30 mL×2), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (S)-tetrahydrofuran-3-yl methanesulfonate 2b as a yellow oil (522 mg, yield 92.5%).

후처리

  1. washwashed with water (30 mL×2)
  2. dry with materialdried with anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e1fb6075bf03430ca64d3ab781cae1be
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139548B2

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