Ethyl Acetate → HCID 19907358, compound

HRID 2371525Notes

Reaction equation

HRID 2371525 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]([C:36](OCC)=[O:37])[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH:25]([C:31](OCC)=[O:32])[C:26](OCC)=[O:27])=[CH:18][CH:17]=1)=O)C.C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[OH:9][CH2:10][CH:12]([CH2:36][OH:37])[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH:25]([CH2:26][OH:27])[CH2:31][OH:32])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19907376HCID 19907376, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19907358HCID 19907358, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

First, 525 mg of lithium aluminium hydride was added to 30 ml of absolute tetrahydrofuran, then 20 ml of a solution of 2.39 g 1,4-bis(4,4-diethoxycarbonylbutyl)benzene in absolute tetrahydrofuran was added dropwise thereto with stirring at a room temperature, and the mixture was refluxed for one hour. After adding 4 ml of ethyl acetate with ice-cooling, the reaction mixture was stirred for 10 minutes. To the mixture were further added successively 0.5 ml of water, 0.5 ml of 15% sodium hydroxide aqueous solution and 1.5 ml of water, and the mixture was stirred for one hour. After filtering off insoluble matter, the filtrate was evaporated under a reduced pressure. The oily residue thus obtained was applied to a silica gel column and eluted with chloroform/ethanol (5:1) to obtain 350 mg of the title compound as a colorless crystal.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred for 10 minutes
  4. stirringthe mixture was stirred for one hour
  5. filtrationAfter filtering off insoluble matter
  6. customthe filtrate was evaporated under a reduced pressure
  7. customThe oily residue thus obtained
  8. washeluted with chloroform/ethanol (5:1)

Sources & evidence

ORD record
ord-bb59fcb4e8b84c02ac48692861632da4
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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