Diethyl Oxalate → Ethyl 4-oxo-8-[(E)-2-[4-(4-phenylbutoxy)phenyl]-ethen-1-yl]-4H-1-benzopyran-2-carboxylate

HRID 1603929Notes

Reaction equation

HRID 1603929 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]3[C:21]([OH:29])=[C:22]([C:26](=[O:28])[CH3:27])[CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:30](OCC)(=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32]>>[O:28]=[C:26]1[C:22]2[CH:23]=[CH:24][CH:25]=[C:20](/[CH:19]=[CH:18]/[C:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:13][CH:14]=3)[C:21]=2[O:29][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27]1

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 196063603'-[(E)-2-[4-(4-Phenylbutoxy)phenyl]ethen-1-yl]-2'-hydroxyacetophenone

Product 1

HCID 19606351Ethyl 4-oxo-8-[(E)-2-[4-(4-phenylbutoxy)phenyl]-ethen-1-yl]-4H-1-benzopyran-2-carboxylateYield 66%

Procedure

Following the process described in example 1 (point A), starting from 3'-[(E)-2-[4-(4-phenylbutoxy)phenyl]-ethen-1-yl]-2'-hydroxyacetophenone and diethyl oxalate, the title compound was prepared, which was purified by chromatography through a silica gel column, eluting with petroleum ether:chloroform, 6:4 (66% yield).

Workup

  1. customwhich was purified by chromatography through a silica gel column
  2. washeluting with petroleum ether

Sources & evidence

ORD record
ord-834728ce6cea4274babff8a3f23d5531
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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