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

HRID 2102306ノート

反応式

HRID 2102306 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e708443af2304e45a4e7c6f3d30204b6
出典データセット
uspto-grants-2009_08
特許番号
US07576077B2

反応ノート

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