Triethylamine → HCID 57857516、化合物

HRID 2266967ノート

反応式

HRID 2266967 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[S:20](Cl)([CH3:23])(=[O:22])=[O:21]>ClCCl>[CH3:23][S:20]([O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:22])=[O:21]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24522Ethyl 3-hydroxybenzoateHCID 31297Methanesulfonyl chloride

生成物 1

HCID 57857516HCID 57857516、化合物収率 55.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of ethyl 3-hydroxybenzoate (3.32 g, 20 mmol) in dichloromethane (20 mL) cooled to 0° C. was added triethylamine (4.17 mL, 30 mmol). To this was added mesyl chloride (1.94 mL, 25 mmol) dropwise over 15 min. The reaction was stirred at 0° C. for 15 min then quenched with water and the phases separated. The aqueous layer was extracted with dichloromethane and the combined organics were dried over MgSO4 and concentrated in vacuo. The crude material was purified via the Biotage SP4 (silica-packed 25+M; 0-50% EtOAc/hexanes) to provide the title compound as a white solid (2.698 g, 55%). 1H NMR (300 MHz, CDCl3) δ: 7.98 (m, 1H), 7.89 (s, 1H), 7.47 (m, 2H), 4.35 (q, J=7.0 Hz, 2H), 3.16 (s, 3H), 1.37 (t, J=7.0 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 165.3, 149.3, 132.9, 130.3, 128.7, 126.9, 123.2, 61.8, 37.8, 14.5 ppm. IR (neat, cm−1): 1721, 1384, 1369, 1268, 1194, 1168, 1098, 936, 840, 798.

後処理

  1. customthen quenched with water
  2. customthe phases separated
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialthe combined organics were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified via the Biotage SP4 (silica-packed 25+M; 0-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ff8c9b7306f3478491af3cc50201b9f9
出典データセット
uspto-grants-2010_12
特許番号
US07858784B2

反応ノート

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