o-Fluorobenzaldehyde → (E)-ethyl 3-(2-fluorophenyl)-2-methylacrylate

HRID 514658ノート

反応式

HRID 514658 の反応式
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([CH2:15][CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13][CH3:14])=[O:11]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[C:15](\[CH3:16])/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

4

反応物 2

HCID 67970o-FluorobenzaldehydeHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

生成物 1

HCID 86632357(E)-ethyl 3-(2-fluorophenyl)-2-methylacrylate収率 126%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

2-Fluorobenzaldehyde (5.0 g, 40.3 mmol) was dissolved in 150 mL toluene. (Carboethoxyethylidene)triphenylphosphorane (42 g; 116 mmol) was added and the mixture was heated to reflux overnight. The solution was cooled, diluted with hexanes, and the solid was filtered. The filtrate was evaporated in vacuo, then dissolved in ether and filtered through a plug of silica gel using ether as eluent. The solvents were evaporated in vacuo to afford the title compound (10.57 g) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.70 (s, 1H), 7.26-7.38 (m, 3H), 7.17 (m, 2H), 4.28 (q, J=7.12 Hz, 2H), 2.04 (s, 3H), 1.35 (t, J=7.12 Hz, 3H).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe solution was cooled
  4. filtrationthe solid was filtered
  5. customThe filtrate was evaporated in vacuo
  6. dissolutiondissolved in ether
  7. filtrationfiltered through a plug of silica gel
  8. customThe solvents were evaporated in vacuo

出典と根拠

ORDレコード
ord-f4119feedcc4419c9ef41bf244ac39c9
出典データセット
uspto-grants-2015_08
特許番号
US09108905B2

反応ノート

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