Triethylamine → Methyl [4-(3-methanesulfonyloxypropyl)phenoxy]acetate

HRID 1700945노트

반응식

HRID 1700945 반응식
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)(=[O:27])=[O:26]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22949949Methyl [4-(3-hydroxypropyl)phenoxy]acetate

생성물 1

HCID 22949950Methyl [4-(3-methanesulfonyloxypropyl)phenoxy]acetate수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of methyl [4-(3-hydroxypropyl)phenoxy]acetate (4.5 g, 20.5 mmol) in dichloromethane (50 ml) was treated at 0° C. with triethylamine (4.36 g, 43.1 mmol) followed by methanesulfonyl chloride (3.99 g, 34.8 mmol) added dropwise over 5 min. After 30 min at 0° C., the reaction mixture was diluted with dichloromethane, washed with 1N hydrochloric acid, water and dried over anhydrous sodium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 8:18) gave 5.51 g (89%) of the title material as a white solid: mp 49-51° C.

후처리

  1. additionadded dropwise over 5 min
  2. washwashed with 1N hydrochloric acid, water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate, 8:18)

출처 및 근거

ORD 기록
ord-3738c5ec6158472393c6b0833dd9c065
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350892B1

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