Diethyl Oxalate → Ethyl Acetate

HRID 1603877Notes

Reaction equation

HRID 1603877 reaction equation
[C:1]([C:4]1[C:5]([OH:32])=[C:6]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][CH:18]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:17][CH2:16]3)=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[C:33](OCC)(=O)[C:34]([O:36][CH2:37][CH3:38])=[O:35]>>[CH2:25]([O:24][CH2:23][CH:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:11]([NH:10][C:6]3[C:5]4[O:32][C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:2][C:1](=[O:3])[C:4]=4[CH:9]=[CH:8][CH:7]=3)=[O:12])[CH:14]=2)[O:19]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1.[C:34]([O:36][CH2:37][CH3:38])(=[O:35])[CH3:33]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 19606371N-(3-acetyl-2-hydroxyphenyl)-2-(benzyloxymethyl)chromane-6-carboxamide

Product 2

HCID 8857Ethyl AcetateYield 66%HCID 19606281Ethyl 8-[2-(benzyloxymethyl)chromane-6-carboxamido]-4-oxo-4H-1-benzopyran-2-carboxylate

Procedure

Following the process described at point A, starting from N-(3-acetyl-2-hydroxyphenyl)-2-(benzyloxymethyl)chromane-6-carboxamide and diethyl oxalate, the title compound was prepared, which was purified by warm crystallization in ethyl acetate (66% yield).

Workup

  1. customwhich was purified
  2. temperatureby warm

Sources & evidence

ORD record
ord-9f384bd90a66428b87d2d2bab5374246
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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