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

HRID 1438178ノート

反応式

HRID 1438178 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ed91220a61e54dd696d95d18e0200e66
出典データセット
uspto-grants-2009_11
特許番号
US07622585B2

反応ノート

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