Boron trifluoride etherate → Ethyl (2E)-4-oxo-4-phenyl-2-butenoate

HRID 982184Notes

Reaction equation

HRID 982184 reaction equation
[C:1](/[CH:9]=[CH:10]\[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[C:1](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 1070335820908-27-4

Product 1

HCID 5369605Ethyl (2E)-4-oxo-4-phenyl-2-butenoateYield 87.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 200 mg of ethyl cis-β-benzoylacrylate, 200 mg of boron trifluoride etherate (about 47 %) and 10 ml of toluene was stirred at 80° C. for 45 minutes and then cooled, followed by the procedure as in Example 1 to give 175 mg of ethyl trans-β-benzoylacrylate as a yellow oil.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-c1ce808d7db64590a56369cb294c846b
Source dataset
uspto-grants-1991_02
Patent number
US04994600

Reaction notes

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