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Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(3-(benzyloxy)-4-methylphenyl)acrylate

HRID 709660
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HRID 709660 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[CH3:17])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:14]=[CH:15][C:16]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

4

반응물 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 161013893-(Benzyloxy)-4-methylbenzaldehyde

생성물 1

HCID 131733900Ethyl 3-(3-(benzyloxy)-4-methylphenyl)acrylate수율 76.3%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
70 °C

실험 절차

Under a nitrogen atmosphere, to a solution of 3-(benzyloxy)-4-methylbenzaldehyde (2.50 g) in toluene (50 mL) was added ethyl (triphenylphosphoranylidene)acetate (4.20 g), and the mixture was stirred at 70° C. for 15 hr. The reaction mixture was concentrated, diethyl ether (100 mL) was added, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.50 g) as a colorless oil. This compound was used for the next step without further purification.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additiondiethyl ether (100 mL) was added
  3. filtrationthe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-50fd903ef6794fcc930d12baf51b1781
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181186B2

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