4-Toluenesulfonyl chloride → (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 452951

반응식

HRID 452951 반응식
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][OH:7].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:7][CH2:6][C@H:2]2[CH2:3][CH2:4][CH2:5][O:1]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

참가 물질

5

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 6931745(2R)-oxolan-2-ylmethanol

생성물 1

HCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate수율 69.4%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

To (R)-(tetrahydrofuran-2-yl)methanol (1.0 g, 9.8 mmol) in CH2Cl2 (3 mL) and pyridine (3 mL) at ambient temperature was added 4-methylbenzene-1-sulfonyl chloride (2.0 g, 10.3 mmol) portion-wise over 5 minutes. This mixture was stirred for 16 hours at ambient temperature then was quenched with 10 mL of 5% aqueous HCl and was extracted with 3×5 mL CH2Cl2. The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 75% hexanes in ethyl acetate) to give the title compound (1.7 g, 6.8 mmol, 69% yield). MS (DCI/NH3) m/z 257 (M+H)+ and 274 (M+NH4)+.

후처리

  1. customthen was quenched with 10 mL of 5% aqueous HCl
  2. extractionwas extracted with 3×5 mL CH2Cl2
  3. dry with materialThe combined organics were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography (SiO2, 75% hexanes in ethyl acetate)

출처 및 근거

ORD 기록
ord-24baeece519a4546a2361079b7e2aebc
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492371B2

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