4-Methyl-3-oxopentanenitrile → 5-Hydroxy-4,4-dimethyl-3-oxopentanenitrile

HRID 631425Notes

Reaction equation

HRID 631425 reaction equation
[Si]([O:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13]C)=O)(C(C)(C)C)(C)C.CC(C)C(=O)[CH2:20][C:21]#[N:22]>>[OH:8][CH2:9][C:10]([CH3:15])([CH3:16])[C:11](=[O:13])[CH2:20][C:21]#[N:22]

Participants

3

Reactant 2

HCID 101299214-Methyl-3-oxopentanenitrileHCID 12044793Methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate

Product 1

HCID 120447945-Hydroxy-4,4-dimethyl-3-oxopentanenitrileYield 29%

Procedure

Prepared from methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate (6 g, 24.39 mmol) according to the method described for 4-methyl-3-oxopentanenitrile Example XA Step 1. Purification via silica gel chromatography eluting with 33% ethyl acetate in petroleum ether afforded 5-hydroxy-4,4-dimethyl-3-oxopentanenitrile as a yellow oil (1 g, 29%). 1H NMR (300 MHz, CDCl3) δ 3.76 (s, 2H), 3.61 (s, 2H), 1.19 (s, 6H).

Workup

  1. customPurification via silica gel chromatography
  2. washeluting with 33% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-91c66e3cbe1d49129ed0a94048032148
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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