Water → Ethyl-m-nitrocinnamate

HRID 1256080

反応式

HRID 1256080 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH2:12]([O:14][C:15](=[O:25])[CH2:16]P(OCC)(OCC)=O)[CH3:13].[H-].[Na+].O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:16][C:15]([O:14][CH2:12][CH3:13])=[O:25])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

生成物 1

HCID 94827Ethyl-m-nitrocinnamate収率 96.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-nitrobenzaldehyde (49 g, 295 mmol) and (diethoxy-phosphoryl)-acetic acid ethyl ester (72.74 g, 325 mmol) in DMF (300 ml) at 0° C. was added NaH (14.2 g, 354 mmol) portionwise and stirred for 1.5 hrs at r.t. The reaction mixture was poured into water to give colorless crystals, which were collected by filtration and washed with water and hexane to give the product ethyl 3-(3-nitrophenyl)acrylate (63 g, yield 96.6%). 1H NMR MeOD 400 MHz. δ 8.42-7.62 (m, 4H), 7.74-7.70 (d, 1H), 6.68-6.64 (d, 1H), 4.28-4.22 (m, 2H), 1.34-1.30 (m, 3H).

後処理

  1. customto give colorless crystals, which
  2. filtrationwere collected by filtration
  3. washwashed with water and hexane

出典と根拠

ORDレコード
ord-bd0fdc0f03f3443c8d05728335aaed51
出典データセット
uspto-grants-2013_06
特許番号
US08461134B2

関連ノート

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