Benzaldehyde → Ethyl cinnamoylacetate

HRID 1906028Notes

Reaction equation

HRID 1906028 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].C(N(CC)CC)C>O1CCCC1.C(Cl)(Cl)(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[O:12]=[C:11]([CH:13]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][C:9]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 8868Ethyl Acetoacetate

Product 1

HCID 54004396Ethyl cinnamoylacetate

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold (5°) solution of 0.015 moles of benzaldehyde and 0.015 moles of ethyl acetoacetate in 60 ml of tetrahydrofuran was added 0.060 mole of triethylamine. After the mixture was stirred for 5 minutes, a solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added dropwise over 10 minutes. The reaction mixture was then stirred for 20 hours, after which the title product was isolated by the extraction and chromatography methods described in Example 1. The material prepared by this procedure was identical to that prepared by the method of Example 1, as indicated by the reverse phase chromatographic method described in Example 2.

Workup

  1. stirringThe reaction mixture was then stirred for 20 hours

Sources & evidence

ORD record
ord-36d4991f3e2c4f2fa266e5fbd3de155e
Source dataset
uspto-grants-1987_03
Patent number
US04649157

Reaction notes

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