Tert-butyl acetoacetate → HCID 54537908, compound

HRID 1086069Notes

Reaction equation

HRID 1086069 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:18](=[C:23]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:19]=[CH:20][CH:21]=[O:22])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>O1CCCC1>[CH:12]1([C:18](=[C:23]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[CH:19]=[CH:20][CH:21]([OH:22])[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][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 54070568HCID 54070568, compound

Product 1

HCID 54537908HCID 54537908, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The dianion of t-butyl acetoacetate (13 mL of 1M solution, 13 mmol; prepared as described in Example 6) was added to a solution of 4-cyclohexyl-5,5-bis(4-fluorophenyl)-2,4-pentadienal (3.75 g, 11 mmol) in tetrahydrofuran at -50° C. After stirring for 2.5 hours the solution was quenched with 2N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 0.5% methanol in methylene chloride to give 4.0 g of the title compound as an oil.

Workup

  1. customwas quenched with 2N hydrochloric acid
  2. extractionthe mixture extracted with diethyl ether
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel eluting with 0.5% methanol in methylene chloride

Sources & evidence

ORD record
ord-4a56cd7340d34cfba559f42cca2df5c8
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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