Ethyl (2E)-3-ethoxy-2-butenoate → (E)-4-(3-chloro-4-cycloheptyl-phenyl)-3-pentene-2-one

HRID 1605667Notes

Reaction equation

HRID 1605667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15](=O)[CH3:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C([O:20]/[C:21](/[CH3:28])=[CH:22]/C(OCC)=O)C>>[Cl:1][C:2]1[CH:3]=[C:4](/[C:15](/[CH3:16])=[CH:22]/[C:21](=[O:20])[CH3:28])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 5354173Ethyl (2E)-3-ethoxy-2-butenoateHCID 214844283'-Chloro-4'-cycloheptyl-acetophenone

Product 1

HCID 68135195(E)-4-(3-chloro-4-cycloheptyl-phenyl)-3-pentene-2-oneYield 51%

Procedure

(E)-4-(3-chloro-4-cycloheptyl-phenyl)-3-pentene-2-one was prepared analogous to Example 52 from 3'-chloro-4'-cycloheptyl-acetophenone (b.p. 136°-139°C at 0.1 mm Hg; nD23 = 1.5572) and ethyl (E)-3-ethoxy-crotonate with a yield of 51% of theory. B.p. 160°-165°C at 0.1 mm Hg.

Sources & evidence

ORD record
ord-7af19697a43b45ee9c7cc221b4f49e0d
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

Loading…