Water → 1-(Hydroxymethyl)cyclopentanecarbonitrile

HRID 2242381Notes

Reaction equation

HRID 2242381 reaction equation
C([O:3][C:4]([C:6]1([C:11]#[N:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[OH:3][CH2:4][C:6]1([C:11]#[N:12])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 15688760Ethyl 1-cyanocyclopentane-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 566871891-(Hydroxymethyl)cyclopentanecarbonitrileYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Cyano-cyclopentanecarboxylic acid ethyl ester (2.00 g, 12.0 mmol) was dissolved in anhydrous tetrahydrofuran (5 ml) under nitrogen and lithium aluminium hydride (36 ml, 36 mmoles, 1.0M in THF) was added dropwise at 0° C. After stirring at room temperature for 24 h water was carefully added to the reaction and the product mixture extracted with ethyl acetate (3×50 ml). The organic layers were combined and washed with water (40 ml) and saturated sodium chloride solution (25 ml). The combined organic phases were dried over magnesium sulphate, filtered and evaporated under reduced pressure to give 1-hydroxymethyl-cyclopentanecarbonitrile (75 mg, 28%) as an oil which solidified on standing to give a waxy yellow solid.

Workup

  1. additionwas carefully added to the reaction
  2. extractionthe product mixture extracted with ethyl acetate (3×50 ml)
  3. washwashed with water (40 ml) and saturated sodium chloride solution (25 ml)
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0ec30203d39749e88c7e7d8cb2d03e7f
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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