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

HRID 514658노트

반응식

HRID 514658 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f4119feedcc4419c9ef41bf244ac39c9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108905B2

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