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

HRID 2365766노트

반응식

HRID 2365766 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].O>C(Cl)Cl>[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

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

생성물 1

HCID 57561588(S)-tetrahydrofuran-3-yl methanesulfonate수율 83.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of (S)-tetrahydrofuran-3-ol (1.0 g, 11 mmol) and triethylamine (9.4 mL, 86 mmol) in CH2Cl2 (20 mL) was cooled in an ice-water bath. To this, methanesulfonyl chloride (3.0 mL, 39 mmol) diluted in CH2Cl2 (10 mL) was added dropwise. The reaction was left stirring for 12 hours at room temperature. Water was added, and organic phases extracted in CH2Cl2 (3×50 mL), which were subsequently dried onto silica and purified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient) to afford (S)-tetrahydrofuran-3-yl methanesulfonate (1.52 g, brown oil, 83% yield).

후처리

  1. additionwas added dropwise
  2. waitThe reaction was left
  3. extractionorganic phases extracted in CH2Cl2 (3×50 mL)
  4. customwhich were subsequently dried onto silica
  5. custompurified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient)

출처 및 근거

ORD 기록
ord-1e0320a797c94a76abaeab62da60a7f5
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697709B2

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