Ethyl (2E)-3-ethoxy-2-butenoate → (E)-4-(3-Bromo-4-cyclohexyl-phenyl)-3-pentene-2-one

HRID 1605664Notes

Reaction equation

HRID 1605664 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14](=O)[CH3:15])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C([O:19]/[C:20](/[CH3:27])=[CH:21]/C(OCC)=O)C>CO>[Br:1][C:2]1[CH:3]=[C:4](/[C:14](/[CH3:15])=[CH:21]/[C:20](=[O:19])[CH3:27])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 5354173Ethyl (2E)-3-ethoxy-2-butenoateHCID 215471453'-Bromo-4'-cyclohexylacetophenone

Product 1

HCID 68134037(E)-4-(3-Bromo-4-cyclohexyl-phenyl)-3-pentene-2-oneYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-4-(3-Bromo-4-cyclohexyl-phenyl)-3-pentene-2-one was prepared analogous to Example 52, from 3'-bromo-4'-cyclohexylacetophenone (b.p. 135°-138°C at 0.15 mm Hg; nD20 = 1.5740) an ethyl (E)-3-ethoxy-crotonate with a yield of 69% of theory. B.p. 170°-175°C at 0.3 mm Hg; m.p. 52°-53°C (from methanol).

Sources & evidence

ORD record
ord-1a14c392d3e74f2d8a6712e9a443216e
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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