Water → HCID 20344133, compound

HRID 2049654Notes

Reaction equation

HRID 2049654 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:9]=[C:10]([C:14](=[O:22])[CH:15]=[C:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[CH:11]=[CH:12][CH:13]=1.O.C1(C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O>O1CCCC1>[CH3:7][C:8]1[CH:9]=[C:10]([C:14](=[O:22])[CH2:15][CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 322000HCID 322000, compoundHCID 4432340PicrateHCID 21226445Aluminium lithium hydride

Product 1

HCID 20344133HCID 20344133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.8 g of lithium aluminum hydride are added portionwise at 0° to 66 g of 1-(3-methylphenyl)-2-(1-methyl-2-pyrrolidinyliden)ethanone dissolved in 550 ml of tetrahydrofuran. 20 minutes after completion of the addition, water is added dropwise until no evolution of gas is any longer observed. The light-yellow organic phase is decanted from the formed precipitate, the latter is extracted with diethyl ether, the united organic phases are dried over sodium sulfate and concentration to an oil is effected. After distillation under vacuum, 61.7 g (92% of theory) of the title compound (b.p. 116° at 0.01 mm Hg) are obtained. Picrate (from ethanol): m.p. 146° to 149°.

Workup

  1. additionis added dropwise until no evolution of gas
  2. customThe light-yellow organic phase is decanted from the formed precipitate
  3. extractionthe latter is extracted with diethyl ether
  4. dry with materialthe united organic phases are dried over sodium sulfate and concentration to an oil
  5. distillationAfter distillation under vacuum, 61.7 g (92% of theory) of the title compound (b.p. 116° at 0.01 mm Hg)
  6. customare obtained

Sources & evidence

ORD record
ord-f78419e6e29d4ee18fd6c875f910ddb8
Source dataset
uspto-grants-1980_04
Patent number
US04198424

Reaction notes

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