Acetoacetic Acid → HCID 15661449, compound

HRID 1885377Notes

Reaction equation

HRID 1885377 reaction equation
Br[CH:2](Br)[C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[CH:8]=[C:9]([Br:17])[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:5][CH:4]=1.[C:19]([O-:22])(=[O:21])[CH3:20].[K+].CC([CH2:27][C:28]([OH:30])=[O:29])=O>CN(C=O)C.C(OCC)(=O)C>[C:19]([O:22][CH:2]([O:30][C:28](=[O:29])[CH3:27])[C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[CH:8]=[C:9]([Br:17])[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:5][CH:4]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 96Acetoacetic AcidHCID 517044Potassium AcetateHCID 15661448HCID 15661448, compound

Product 1

HCID 15661449HCID 15661449, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To 7-dibromomethyl-3-bromo-9-fluorenone (137.1 mg) in DMF (3.3 ml) was added potassium acetate (78 mg). The reaction mixture was stirred at 100° C. for 70 minutes. It was then diluted with ethyl acetate, washed four times with H2O, twice with brine, dried and evaporated. The residue was purified by preparative tlc using 1% ethyl acetate/methylene chloride gave a mixture of the diacetate and the ultimately desired aldehyde (68.4 mg).

Workup

  1. washwashed four times with H2O
  2. dry with materialtwice with brine, dried
  3. customevaporated
  4. customThe residue was purified by preparative tlc
  5. customgave

Sources & evidence

ORD record
ord-4648d5d7ec68478eac9e6b315ff05910
Source dataset
uspto-grants-1992_09
Patent number
US05144028

Reaction notes

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