Water → HCID 58281299, compound

HRID 552325Notes

Reaction equation

HRID 552325 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]([CH2:11][C:12]#[N:13])[CH2:6][C:7](OC)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[OH:2][CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][OH:8])[CH2:11][C:12]#[N:13]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59843343Dimethyl 3-(cyanomethyl)pentanedioate

Product 1

HCID 58281299HCID 58281299, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, 3-cyanomethyl-pentanedioic acid dimethyl ester (212 g) was added to a suspension of LiAlH4 (50.0 g) in THF (1.8 L) at −20° C. After stirring for 30 min., H2O (200 mL) was slowly added to the reaction mixture. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure to obtain 5-hydroxy-3-(2-hydroxy-ethyl)-pentanenitrile (131 g). 1H NMR (200 MHz, CDCl3) δ ppm 1.38-1.91 (m, 4 H) 1.98-2.36 (m, 1 H) 2.50 (d, J=5.71 Hz, 2 H) 3.51-3.90 (m, 4 H).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-be2acfca88114277a951b9b89e9c200e
Source dataset
uspto-grants-2011_05
Patent number
US07951811B2

Reaction notes

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