Water → (3-pyrrolidin-1-ylphenyl)methanol

HRID 2254452Notes

Reaction equation

HRID 2254452 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([N:12]2[C:16](=O)[CH2:15][CH2:14][C:13]2=O)[CH:9]=[CH:10][CH:11]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[N:12]1([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[CH2:4][OH:3])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 19744713HCID 19744713, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 7162062(3-pyrrolidin-1-ylphenyl)methanolYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

0.25 g of N-(3-ethoxycarbonylphenyl)succinimide [synthesized by heat condensing ethyl m-aminobenzoate with succinic anhydride in acetic acid] was dissolved in 5 ml of anhydrous tetrahydrofuran, and with stirring under ice cooling, 0.17 g of lithium aluminium hydride was added. The mixture was maintained at room temperature for 30 minutes, and then heated under reflux for 4 hours. After the reaction, ethyl acetate and water were added. The organic layer was separated, and then worked up in a customary manner and purified by medium-pressure liquid chromatography [Lobar column, size B, Lichroprep Si 60 (E. Merck & Co.); eluting solvent: hexane/ethyl acetate=10/1) to give 84 mg (yield 47%) of the captioned compound as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. additionwere added
  4. customThe organic layer was separated
  5. custompurified by medium-pressure liquid chromatography [Lobar column, size B, Lichroprep Si 60 (E. Merck & Co.)

Sources & evidence

ORD record
ord-c07a40c838214eb0b000d94f5683e2b3
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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