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Dimethyl Sulfoxide → Methyl 2-(2-nitrophenyl)propanoate

HRID 472494
ノート
印刷プレビュー

反応式

HRID 472494 の反応式
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].IC.[CH3:17]S(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:1][O:2][C:3](=[O:14])[CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])[CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 520464Methyl 2-(2-nitrophenyl)acetate

生成物 1

HCID 12816936Methyl 2-(2-nitrophenyl)propanoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A round bottom flask was charged with (2-nitro-phenyl)-acetic acid methyl ester (4.22 g, 21.6 mmol) (prepared as described in Organic Letters, 2009, 11, 1345-1348), iodomethane (2.8 mL, 45 mmol) and dry dimethyl sulfoxide (20 mL). Cesium carbonate (18 g, 56 mmol) was added and the mixture was stirred at room temperature under an atmosphere of nitrogen for 18 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with water (2×30 mL), saturated aqueous sodium chloride (30 mL), dried over magnesium sulfate, filtered and evaporated. 2-(2-Nitro-phenyl)-propionic acid methyl ester was isolated as a red oil (3.24 g, 71%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.93 (d, J=8.1 Hz, 1H), 7.60 (t, J=7.6 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 4.32 (q, J=7.0 Hz, 1H), 3.67 (s, 3H), 1.61 (d, J=7.0 Hz, 3H). MS=232 (MH)+.

後処理

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. washThe combined organic layers were washed with water (2×30 mL), saturated aqueous sodium chloride (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-8a168fe4e74f48409d186127174607a2
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08633173B2

反応ノート

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