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

HRID 1605665Notes

Reaction equation

HRID 1605665 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12](=O)[CH3:13])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]([CH3:11])[CH3:10].C([O:17]/[C:18](/[CH3:25])=[CH:19]/C(OCC)=O)C>>[Cl:1][C:2]1[CH:3]=[C:4](/[C:12](/[CH3:13])=[CH:19]/[C:18](=[O:17])[CH3:25])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 5354173Ethyl (2E)-3-ethoxy-2-butenoateHCID 215471633'-Chloro-4'-isobutyl-acetophenone

Product 1

HCID 21547103(E)-4-(3-chloro-4-isobutyl-phenyl)-3-pentene-2-oneYield 61%

Procedure

(E)-4-(3-chloro-4-isobutyl-phenyl)-3-pentene-2-one was prepared analogous to Example 52 from 3'-chloro-4'-isobutyl-acetophenone (b.p. 89°-93°C at 0.2 mm Hg) and ethyl (E)-3-ethoxy-crotonate with a yield of 61% of theory (after chromatographic purification on silicagel using petroleum-ether/benzene in a volume ratio of 1:1 as eluant). Colorless oil.

Workup

  1. customafter chromatographic purification on silicagel

Sources & evidence

ORD record
ord-29b1e2e4c5594caeac03e9bf4092dafb
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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