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

HRID 1603934Notes

Reaction equation

HRID 1603934 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]3[C:22]([OH:30])=[C:23]([C:27](=[O:29])[CH3:28])[CH:24]=[CH:25][CH:26]=3)=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:31](OCC)(=O)[C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]3[C:22]4[O:30][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:28][C:27](=[O:29])[C:23]=4[CH:24]=[CH:25][CH:26]=3)=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 196063273'-[(E)-2-[4-[4-(4-Fluorophenyl)butoxy]phenyl]ethen-1-yl]-2'-hydroxyacetophenone

Product 1

HCID 19606308Ethyl 8-[(E)-2-[4-[4-(4-fluorophenyl)butoxy]phenyl]-ethen-1-yl]-4-oxo-4H-1-benzopyran-2-carboxylateYield 65%

Procedure

Following the process described in example 1 (point A), starting from 3'-[(E)-2-[4-[4-(4-fluorophenyl)butoxy]phenyl]ethen-1-yl]-2'-hydroxy-acetophenone and diethyl oxalate, the title compound was prepared, which was purified by chromatography through a silica gel column, eluting with petroleum ether:chloroform, 8:2 (65% yield).

Workup

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

Sources & evidence

ORD record
ord-9bc0e830048e4411bd4ff00aeb295f8c
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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