Water → HCID 58281299, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe insoluble material was removed by filtration
- 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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