Ethyl oxoacetate → HCID 68535649, compound

HRID 2389372Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]([CH3:11])=[O:10])=[CH:4][CH:3]=1.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[O:21]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:9](=[O:10])[CH2:11][CH:20]([OH:21])[C:19]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 70211Ethyl oxoacetate

HCID 15571171HCID 15571171, compound

Product 1

HCID 68535649HCID 68535649, compoundYield 23.6%

Conditions

Temperature: 130 °C

Procedure

A mixture of 1,1-bis(4-fluorophenyl)acetone (2.4 g) and ethyl glyoxylate (47% solution in toluene, 2.1 g) was stirred at 130° C. for 3 days. The reaction mixture was cooled to ambient temperature. The mixture was purified by silica gel column chromatography (n-hexane:EtOAc=4:1) to give ethyl 5,5-bis(4-fluorophenyl)-2-hydroxy-4-oxopentanoate (800 mg) as a brown oil.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
customThe mixture was purified by silica gel column chromatography (n-hexane:EtOAc=4:1)

Sources & evidence

ORD record: ord-1cf6c2608e8a468f813ee4e8e2c325b5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273745B2

Reaction notes

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