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

HRID 62837

Reaction equation

HRID 62837 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-76ce6663f0764a9fa978df089572bfa1
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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