Benzaldehyde, 4-(phenylmethoxy)- → (E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylate

HRID 62837

반응식

HRID 62837 반응식
[C:1]([CH2:6][CH:7]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:4]([O:3][C:1](=[O:2])/[C:6](/[CH3:7])=[CH:39]/[C:38]1[CH:41]=[CH:42][C:35]([O:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:36][CH:37]=1)[CH3:5]

참가 물질

4

반응물 2

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

생성물 1

HCID 12235562(E)-Ethyl 3-(4-(benzyloxy)phenyl)-2-methylacrylate수율 97.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Carbethoxyethylidene triphenylphosphorane (1.02 g, 2.81 mmol) was dissolved in anhydrous THF (25 mL), and 4-benzyloxy-benzaldehyde (0.5 g, 2.36 mmol)/THF (10 mL) solution was added dropwise thereto at −78° C. The mixture was heated slowly to room temperature and then stirred for 12 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure. The residue was added with water and then extracted with EtOAc. The organic layer was dried with MgSO4 and purified by column chromatography (eluent, EtOAc/Hex=1/9) to obtain the title compound (0.68 g, 97.4%).

후처리

  1. customat −78° C
  2. customAfter the termination of the reaction
  3. concentrationthe reactant was concentrated under reduced pressure
  4. additionThe residue was added with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried with MgSO4
  7. custompurified by column chromatography (eluent, EtOAc/Hex=1/9)

출처 및 근거

ORD 기록
ord-76ce6663f0764a9fa978df089572bfa1
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447044B2

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