Acetic Acid → HCID 18355461, compound

HRID 429335Notes

Reaction equation

HRID 429335 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]([C:9]1[O:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[CH:13]=1)=O)=[O:5])[CH3:2].[BH4-].[Na+].C(O)(=O)C>C(O)C.O.[Pd]>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[CH:13]=[C:9]1[CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride2×HCID 12777066Ethyl 3-(1-benzofuran-2-yl)-3-oxopropanoate

Product 1

HCID 18355461HCID 18355461, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

232 g of compound 3 are dissolved in 500 ml of ethanol. Cool in ice-bath and add 100 g of sodium borohydride in 500 ml of water. Stir for 2 hours. Add acetic acid until the sodium borohydride has been neutralized. Cool the solution in ice-bath under an atmosphere of nitrogen and add 10 g of 10% Pd/C catalyst. Stir under a hydrogen atmosphere at 15PSI until the reaction is complete, as judged by TLC. Filter through celite and evaporate organic solvents. Extract with ethyl acetate. Dry over sodium sulfate. Filter. Evaporate solvent.

Workup

  1. temperatureCool in ice-bath
  2. temperatureCool the solution in ice-bath under an atmosphere of nitrogen
  3. stirringStir under a hydrogen atmosphere at 15PSI until the reaction
  4. filtrationFilter through celite
  5. customevaporate organic solvents
  6. extractionExtract with ethyl acetate
  7. dry with materialDry over sodium sulfate
  8. filtrationFilter

Sources & evidence

ORD record
ord-5ef3d64006d046358df24148c5752c4e
Source dataset
uspto-grants-2001_11
Patent number
US06316487B1

Reaction notes

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