Triethylamine → [5-(3-Chlorophenyl)isoxazol-3-yl]methyl methanesulfonate

HRID 2102306노트

반응식

HRID 2102306 반응식
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[O:24][N:23]=[C:22]([CH2:25][OH:26])[CH:21]=2)[CH:17]=[CH:18][CH:19]=1>ClCCl>[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[O:24][N:23]=[C:22]([CH2:25][O:26][S:9]([CH3:8])(=[O:11])=[O:10])[CH:21]=2)[CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanol

생성물 1

HCID 57838012[5-(3-Chlorophenyl)isoxazol-3-yl]methyl methanesulfonate수율 101.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethyl amine (965 mg, 9.5 mmol) and methanesulfonyl chloride (820 mg, 7.2 mmol) were added to a solution of [5-(3-chloro-phenyl)-isoxazol-3-yl]-methanol (1.0 g, 4.8 mmol) in dichloromethane (50 mL) at 0° C. After 1 hour, the reaction mixture was quenched with cold saturated sodium bicarbonate and then the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford methanesulfonic acid 5-(3-chloro-phenyl)-isoxazol-3-ylmethyl ester (1.4 g, 100%, light brown solid). 1H NMR (CDCl3) δ (ppm): 7.80 (s, 1H), 7.70 (m, 1H), 7.45 (m, 2H), 6.73 (s, 1H), 5.37 (s, 2H), 3.16 (s, 3H).

후처리

  1. customthe reaction mixture was quenched with cold saturated sodium bicarbonate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e708443af2304e45a4e7c6f3d30204b6
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576077B2

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