Water → 1-(3-Methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)ethanone

HRID 2049653

Reaction equation

HRID 2049653 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:23])[CH:16]=[C:17]2[CH2:21][CH2:20][CH2:19][N:18]2[CH3:22])[CH:12]=[CH:13][CH:14]=1.O.C(OCC)C>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:23])[CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[CH3:22])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 571537451-(3-Methoxyphenyl)-2-(1-methyl-2-pyrrolidinyliden)ethanone

Product 1

HCID 203441421-(3-Methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11.8 g of lithium aluminum hydride are added portionwise at 0° with stirring to 144.8 g of 1-(3-methoxyphenyl)-2-(1-methyl-2-pyrrolidinyliden)ethanone dissolved in 1.4 liters of tetrahydrofuran. 30 minutes after completion of the addition, 300 ml of water are cautiously added dropwise, with cooling; then 800 ml of diethyl ether are added, and the organic phase is collected. The organic phase is dried over sodium sulfate, the solvent is removed by evaporation, and the oily residue is distilled under a vacuum to obtain 127 g (87% of theory) of the title compound:

Workup

  1. additionare cautiously added dropwise
  2. temperaturewith cooling
  3. customthe organic phase is collected
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed by evaporation
  6. distillationthe oily residue is distilled under a vacuum

Sources & evidence

ORD record
ord-7820fc9e1cab48449fbfec1eb3cd7a56
Source dataset
uspto-grants-1980_04
Patent number
US04198424

Linked notes

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