Tert-butyl acetoacetate → HCID 73657751, compound

HRID 1086077Notes

Reaction equation

HRID 1086077 reaction equation
[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[C:20]([CH:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:21]=[CH:22][CH:23]=[O:24])=[CH:15][CH:14]=1>O1CCCC1>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)=[C:20]([CH:25]([CH:29]([CH3:30])[CH3:31])[CH:26]([CH3:28])[CH3:27])[CH:21]=[CH:22][CH:23]([OH:24])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 72745784HCID 72745784, compound

Product 1

HCID 73657751HCID 73657751, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the dianion of 1,1-dimethylethyl acetoacetate (15 mL of 1M solution, 15 mmol) was added to a solution of 5,5-bis(4-fluorophenyl)-4-[2-methyl-1-(1-methylethyl)propyl]-2,4-pentadienal (4.1 g, 11.1 mmol) in tetrahydrofuran at -60° C. After stirring for 3 hours the reaction was quenched with 2N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 5% ethyl acetate in hexane to give 3.2 g of the title compound as an oil. MS(CI): m/e =526 for M+ of C32H40F2O4.

Workup

  1. customwas quenched with 2N hydrochloric acid
  2. extractionthe mixture extracted with diethyl ether
  3. dry with materialThe extracts were dried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica eluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-eb0ab994b4df43b68546600829ec08e0
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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