Diethyl Oxalate → Ethanol

HRID 1603899Notes

Reaction equation

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

Participants

Reactant 2

HCID 7268Diethyl Oxalate

HCID 19606298HCID 19606298, compound

Product 2

HCID 702EthanolYield 73%

HCID 19606283HCID 19606283, compound

Procedure

Following the process described in example 1 (point A), starting from N-(3-acetyl-2-hydroxyphenyl)-2-benzyloxymethyl-2,3-dihydrobenzofuran-5-carboxamide and diethyl oxalate, the title compound was prepared as a yellow solid with melting point 166-168° C. and purified by crystallization in ethanol (73% yield).

Sources & evidence

ORD record: ord-5bc5d74c8eb244a3bc4e519c19b210c1
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990142

Reaction notes

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