Tert-butyl acetoacetate → HCID 54107373, compound

HRID 1086090Notes

Reaction equation

[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH:12]1([C:15](=[C:20]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:16]=[CH:17][CH:18]=[O:19])[CH2:14][CH2:13]1>O1CCCC1>[CH:12]1([C:15](=[C:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH:16]=[CH:17][CH:18]([OH:19])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:13][CH2:14]1

Participants

Conditions

Temperature: -70 °C

Procedure

The dianion of 1,1-dimethylethyl acetoacetate (22 mL of 0.5M solution, 11 mmol) was added to a solution of 4-cyclopropyl-5,5-bis(4-fluorophenyl)-2,4-pentadienal (2.0 g, 9.7 mmol) in 30 mL tetrahydrofuran at -70° C. The mixture was stirred for 2.5 hours at -70° C. and quenched with saturated ammonium chloride solution. The mixture was extracted with diethyl ether; the extracts were dried over magnesium sulfate and concentrated in vacuo to give 3,0 g of the title compound as an oil. MS(CI): m/e =468 for M+ of C28H30F2O4.

Workup

customquenched with saturated ammonium chloride solution
extractionThe mixture was extracted with diethyl ether
dry with materialthe extracts were dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fb6064960a4441608dceb3da5eb14f75
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05011947

Reaction notes

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