3-Butenenitrile, 2-(acetyloxy)- → Isobutyl (3-(acetyloxy)-3-cyanopropyl)methylphosphinate

HRID 745456Notes

Reaction equation

HRID 745456 reaction equation
[CH3:1][P:2]([O-:8])[O:3][CH2:4][CH:5]([CH3:7])[CH3:6].[CH3:9][C:10]([O:12][CH:13]([C:16]#[N:17])[CH:14]=[CH2:15])=[O:11]>>[C:10]([O:12][CH:13]([C:16]#[N:17])[CH2:14][CH2:15][P:2]([CH3:1])(=[O:8])[O:3][CH2:4][CH:5]([CH3:7])[CH3:6])(=[O:11])[CH3:9]

Participants

3

Reactant 2

HCID 858913-Butenenitrile, 2-(acetyloxy)-HCID 86741778Isobutyl methanephosphonite

Product 1

HCID 44149733Isobutyl (3-(acetyloxy)-3-cyanopropyl)methylphosphinateYield 100.9%

Conditions

Temperature
80 °C

Procedure

208 g of isobutyl methanephosphonite are heated to 80° C. under nitrogen. 0.5 g of tert.-butyl perpivalate is added to the hot reaction solution, and 63.9 g of acrolein cyanohydrin acetate and 2.5 g of tert.-butyl perpivalate are added dropwise within 2.3 hours. The mixture is stirred at 80° C. for 5 min, and 133.9 g of isobutyl methanephosphonite are distilled out under high vacuum (recovery: 91.3%; purity: 97%). 134.6 g of isobutyl (3-acetoxy-3-cyanopropyl)methylphosphinate (yield: 97.8%, purity 95%) are obtained.

Workup

  1. additionare added dropwise within 2.3 hours
  2. distillation133.9 g of isobutyl methanephosphonite are distilled out under high vacuum (recovery: 91.3%; purity: 97%)

Sources & evidence

ORD record
ord-180f8e4ded9d4f7484ad4ea3f7ea779a
Source dataset
uspto-grants-1986_07
Patent number
US04599207

Reaction notes

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