Triethylamine → Benzyl 2-chloro-2-(3,4-dimethoxyphenyl)acetate

HRID 1438178노트

반응식

HRID 1438178 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11](O)[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.S([Cl:34])(C)(=O)=O>C(Cl)Cl>[Cl:34][CH:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57448185Benzyl 2-(3,4-dimethoxyphenyl)-2-hydroxyacetate

생성물 1

HCID 57448186Benzyl 2-chloro-2-(3,4-dimethoxyphenyl)acetate수율 56%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 137D (450 mg, 1.5 mmol) in CH2Cl2 (5 mL) at 0° C. was added triethylamine (0.42 mL, 3.0 mmol) followed by mesyl chloride (0.14 mL, 1.8 mmol). After stirring at rt overnight, the reaction was concentrated and purified via silica gel chromatography (0-25% ethyl acetate/hexanes) to provide 137E (268 mg, 56%). 1H NMR (400 MHz, Methanol-d4) δ ppm 3.81 (s, 3H) 3.87 (s, 3H) 5.19 (m, 2H) 5.36 (s, 1H) 6.81 (d, J=8.35 Hz, 1H) 6.93-7.07 (m, 2H) 7.20-7.42 (m, 5H).

후처리

  1. concentrationthe reaction was concentrated
  2. custompurified via silica gel chromatography (0-25% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-ed91220a61e54dd696d95d18e0200e66
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622585B2

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