Diethyl Oxalate → Ethanol

HRID 1603907Notes

Reaction equation

[C:1]([C:4]1[C:5]([OH:32])=[C:6]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:21][CH:20]([CH2:22][CH2:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:19][C:18]=3[CH:31]=2)=[O:13])[CH:7]=[C:8]([F:10])[CH:9]=1)(=[O:3])[CH3:2].[C:33](OCC)(=O)[C:34]([O:36][CH2:37][CH3:38])=[O:35]>>[C:25]1([CH2:24][CH2:23][CH2:22][CH:20]2[CH2:19][C:18]3[CH:31]=[C:14]([C:12]([NH:11][C:6]4[C:5]5[O:32][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:2][C:1](=[O:3])[C:4]=5[CH:9]=[C:8]([F:10])[CH:7]=4)=[O:13])[CH:15]=[CH:16][C:17]=3[O:21]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH2:1]([OH:3])[CH3:2]

Participants

Reactant 2

HCID 7268Diethyl Oxalate

HCID 19606348HCID 19606348, compound

Product 2

HCID 702EthanolYield 55%

HCID 19606340HCID 19606340, compound

Procedure

Following the process described in example 1 (point A), starting from N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-2-(3-phenylpropyl)-2,3-dihydrobenzofuran-5-carboxamide and diethyl oxalate, the title compound was prepared, which was purified by crystallization in ethanol (55% yield).

Sources & evidence

ORD record: ord-bd9c194321024850889bdedc284aaa01
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990142

Reaction notes

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