Tert-butyl acetoacetate → 1,1-Dimethylethyl 8-ethyl-9,9-bis(4-fluorophenyl)-5-hydroxy-3-oxo-6,8-nondienoate

HRID 1086096Notes

Reaction equation

HRID 1086096 reaction equation
[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH2:12]([C:14](=[C:19]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH:15]=[CH:16][CH:17]=[O:18])[CH3:13]>O1CCCC1>[CH2:12]([C:14](=[C:19]([C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[CH:15]=[CH:16][CH:17]([OH:18])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH3:13]

Participants

4

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 541186354-Ethyl-5,5-bis(4-fluorophenyl)-2,4-pentadienal

Product 1

HCID 736577601,1-Dimethylethyl 8-ethyl-9,9-bis(4-fluorophenyl)-5-hydroxy-3-oxo-6,8-nondienoateYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The dianion of 1,1-dimethylethyl acetoacetate (20 mL of 0.5 M solution, 10 mmol) was added to a solution of 4-ethyl- 5,5-bis-(4-fluorophenyl)-2,4-pentadienal (2.0 g, 6.7 mmol) in 20 mL of tetrahydrofuran at -70° C. The mixture was stirred for 3 hours during which time the temperature was allowed to rise to -30° C. and quenched with saturated ammonium chloride solution. The mixture was extracted with diethyl ether, the extracts dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 10% ethyl acetate in hexane to give 2.2 g of the title compound as an oil. MS(CI): m/e =456 for M+ of C27H30F2O4.

Workup

  1. customto rise to -30° C.
  2. customquenched with saturated ammonium chloride solution
  3. extractionThe mixture was extracted with diethyl ether
  4. dry with materialthe extracts dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bd4dc21c3e3a43b395a7d3ecc26befd3
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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