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

HRID 1700945ノート

反応式

HRID 1700945 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3738c5ec6158472393c6b0833dd9c065
出典データセット
uspto-grants-2002_02
特許番号
US06350892B1

反応ノート

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