Diethyl Oxalate → HCID 178473087, compound

HRID 915459Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].[Na]>>[CH2:19]([O:18][C:16](=[O:17])/[C:15](/[OH:21])=[CH:9]/[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:11]([F:12])([F:13])[F:14])[CH:4]=1)=[O:10])[CH3:20]

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenone

HCID 5360545Sodium

Product 1

HCID 178473087HCID 178473087, compound

Procedure

In analogy to the procedure described for example 11 a], 1-(4-fluoro-3-trifluoromethyl-phenyl)-ethanone was reacted with diethyl oxalate in the presence of metallic sodium to give (Z)-4-(4-fluoro-3-trifluoromethyl-phenyl)-2-hydroxy-4-oxo-but-2-enoic acid ethyl ester as colorless solid.

Sources & evidence

ORD record: ord-09b5c003d8cf4b0bb09515f0755ba42c
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265149B2

Reaction notes

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