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

HRID 1917860Notes

Reaction equation

HRID 1917860 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH3:10])([CH3:9])[C:5](OC)=[O:6].CC(C)C(=O)[CH2:14][C:15]#[N:16]>>[CH3:1][O:2][CH2:3][C:4]([CH3:10])([CH3:9])[C:5](=[O:6])[CH2:14][C:15]#[N:16]

Participants

3

Reactant 2

HCID 101299214-Methyl-3-oxopentanenitrileHCID 14302192Methyl 3-methoxy-2,2-dimethylpropanoate

Product 1

HCID 108989285-Methoxy-4,4-dimethyl-3-oxopentanenitrileYield 29%

Procedure

Prepared from methyl 3-methoxy-2,2-dimethylpropanoate (8 g, 54.7 mmol) according to the method described in Example 122A Step 1 for 4-methyl-3-oxopentanenitrile. Purification via silica gel chromatography eluting with mixtures of petroleum ether and ethyl acetate afforded 5-methoxy-4,4-dimethyl-3-oxopentanenitrile as a yellow oil (2.5 g, 29%). 1H NMR (300 MHz, CDCl3) δ 3.72 (s, 2H), 3.32-3.33 (m, 5H), 1.18 (s, 6H).

Workup

  1. customPurification via silica gel chromatography
  2. washeluting with mixtures of petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-f742e00e13cb4b079a79e25d545c401c
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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