Hydride → HCID 19025025, compound

HRID 1033938Notes

Reaction equation

HRID 1033938 reaction equation
[CH3:1][C:2]1[CH2:6][N:5]([C:7]([CH3:14])([CH3:13])[C:8](OCC)=[O:9])[C:4](=[O:15])[C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Li].[H-]>O1CCCC1>[CH3:14][C:7]([N:5]1[CH2:6][C:2]([CH3:1])=[C:3]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4]1=[O:15])([CH3:13])[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 166653HydrideHCID 3028194LithiumHCID 19025023HCID 19025023, compound

Product 1

HCID 19025025HCID 19025025, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

52.4 g (200 mmol) of ethyl 2-(4-methyl-2-oxo-3-phenyl-3-pyrrolin-1-yl)isobutyrate was dissolved in 300 ml of tetrahydrofuran, and the solution was cooled to -30° C. In a dropping funnel, 7.6 g (200 mmol) of lithium alminum hydride was suspended in 100 ml of tetrahydrofuran, and the suspension was dropwise added at -30° C. After completion of the dropwise addition, the cooling medium was removed, and a suitable amount of water was added, and excess of lithium aluminum hydride was quenched. Insoluble material was removed by filtration, and the filtrate was concentrated and the solid thus obtained was washed with isoproyl ether to obtain 40.9 g (yield: 83%) of the desired product having a melting point of from 77° to 78° C.

Workup

  1. additionthe suspension was dropwise added at -30° C
  2. additionAfter completion of the dropwise addition
  3. customthe cooling medium was removed
  4. additiona suitable amount of water was added
  5. customexcess of lithium aluminum hydride was quenched
  6. customInsoluble material was removed by filtration
  7. concentrationthe filtrate was concentrated
  8. customthe solid thus obtained
  9. washwas washed with isoproyl ether

Sources & evidence

ORD record
ord-7f8adac5b1c14dccb772c5b78a400617
Source dataset
uspto-grants-1994_05
Patent number
US05312929

Reaction notes

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