Triethylamine → HCID 57857516, 화합물

HRID 2266967노트

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HRID 2266967 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 24522Ethyl 3-hydroxybenzoateHCID 31297Methanesulfonyl chloride

생성물 1

HCID 57857516HCID 57857516, 화합물수율 55.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ff8c9b7306f3478491af3cc50201b9f9
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858784B2

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