Ethanol → HCID 74011442, compound

HRID 362464Notes

Reaction equation

HRID 362464 reaction equation
C(O)C.[O:4]=[C:5]([N:25]1[CH2:29][C:28]2=[CH:30][O:31][CH:32]=[C:27]2[CH2:26]1)[CH2:6][CH:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([O:10]CC1C=CC=CC=1)=[O:9].[OH-].[Na+]>O1CCCC1.O>[O:4]=[C:5]([N:25]1[CH2:26][C:27]2=[CH:32][O:31][CH:30]=[C:28]2[CH2:29]1)[CH2:6][CH:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 74011447HCID 74011447, compound

Product 1

HCID 74011442HCID 74011442, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

10 ml of ethanol are added to a solution of 1 g (2.56 mmol) of phenylmethyl γ-oxo-α(R,S)-(phenylmethyl)-5,6-dihydro-4H-furo[3,4-c]pyrrole-5-butanoate in 10 ml of tetrahydrofuran followed, at 0° C., by a solution of 0.308 g (7.7 mmol) of sodium hydroxide in 10 ml of water. The mixture is stirred for 2 h at 0° C., and then for 2 h at room temperature. The solution obtained is concentrated, 30 ml of water are added and the solution is washed with twice 35 ml of diethyl ether. The aqueous phase is cooled, and then a 2M solution of hydrochloric acid is added to pH 2. The precipitate formed is filtered, it is washed with twice 20 ml of water and it is dried under vacuum. 0.47 g of a white solid is obtained. Yield 61%.

Workup

  1. waitfor 2 h at room temperature
  2. customThe solution obtained
  3. concentrationis concentrated
  4. addition30 ml of water are added
  5. washthe solution is washed with twice 35 ml of diethyl ether
  6. temperatureThe aqueous phase is cooled
  7. additiona 2M solution of hydrochloric acid is added to pH 2
  8. customThe precipitate formed
  9. filtrationis filtered
  10. washit is washed with twice 20 ml of water and it
  11. customis dried under vacuum

Sources & evidence

ORD record
ord-cc455c80bb20454b9f9dbc6ee257ef02
Source dataset
uspto-grants-1999_02
Patent number
US05869518

Reaction notes

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