Benzaldehyde → Ethyl cinnamoylacetate

HRID 1906029Notes

Reaction equation

HRID 1906029 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl.O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[O:4]=[C:3]([CH:5]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 8868Ethyl Acetoacetate

Product 1

HCID 54004396Ethyl cinnamoylacetate

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.020 moles of titanium tetrachloride in 15 ml of carbon tetrachloride was added over a period of 10 minutes to a cold (5°) solution of 0.015 moles of ethyl acetoacetate and 0.015 moles of benzaldehyde in 60 ml of tetrahydrofuran. After the mixture was stirred for 1.5 hours, a solution of 0.060 mole of triethylamine in 15 ml of tetrahydrofuran was added dropwise. The reaction mixture was then stirred for 20 hours, after which the title compound 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-45b898ccc5bd420f8b7bbb63e2f81564
Source dataset
uspto-grants-1987_03
Patent number
US04649157

Reaction notes

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