Triethylamine → (2R)-2-methoxypropyl 4-methylbenzene-1-sulfonate

HRID 339088노트

반응식

HRID 339088 반응식
[CH3:1][O:2][C@H:3]([CH3:6])[CH2:4][OH:5].[CH3:7]CN(CC)CC.[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1>C(Cl)Cl>[CH3:7][C:18]1[CH:19]=[CH:14][C:15]([S:20]([O:5][CH2:4][C@H:3]([O:2][CH3:1])[CH3:6])(=[O:21])=[O:22])=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 27335882-Methoxy-1-propanol, (2R)-

생성물 1

HCID 13896527(2R)-2-methoxypropyl 4-methylbenzene-1-sulfonate수율 55.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a stirred solution of crude (R)-2-methoxypropan-1-ol (4.30 g, 47.7 mmol) in DCM (200 mL) was added Et3N (10.0 mL, 71.6 mmol). A solution of toluene sulfonyl chloride (10.9 g, 57.3 mmol) in DCM (80 mL) was added dropwise at 0° C. under nitrogen. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction was diluted with DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 10:1 to 4:1) to give (R)-2-methoxypropyl 4-methylbenzenesulfonate (6.43 g, 55% for three steps).

후처리

  1. washwashed with saturated aqueous NaHCO3 solution and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 10:1 to 4:1)

출처 및 근거

ORD 기록
ord-8da25985801e481ab8f216b901773cd4
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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