3-Butenenitrile, 2-(acetyloxy)- → Isopentyl (3-acetoxy-3-cyanopropyl)methylphosphinate

HRID 745458Notes

Reaction equation

HRID 745458 reaction equation
[CH3:1][P:2]([O-:9])[O:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[CH3:10][C:11]([O:13][CH:14]([C:17]#[N:18])[CH:15]=[CH2:16])=[O:12]>>[C:11]([O:13][CH:14]([C:17]#[N:18])[CH2:15][CH2:16][P:2]([CH3:1])(=[O:9])[O:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])(=[O:12])[CH3:10]

Participants

3

Reactant 2

HCID 858913-Butenenitrile, 2-(acetyloxy)-HCID 131714779Isopentyl methanephosphonite

Product 1

HCID 54245807Isopentyl (3-acetoxy-3-cyanopropyl)methylphosphinateYield 100.9%

Conditions

Temperature
80 °C

Procedure

235.0 g of isopentyl methanephosphonite are heated to 80° C. under nitrogen, and 0.5 g of tert.-butyl perpivalate is added. 63.9 g of acrolein cyanohydrin acetate and 2.5 g of tert.-butyl perpivalate are added drop-wise, with vigorous stirring at 80° C., within 3 hours. After reaction is complete, 155.2 g of 97.5% pure isopentyl methanephosphonite are distilled out under high vacuum. (Recovery: 95%). 141.8 g of isopentyl (3-acetoxy-3-cyanopropyl)methylphosphinate (yield=96.5%; purity=93.6%) are obtained.

Workup

  1. addition0.5 g of tert.-butyl perpivalate is added
  2. customAfter reaction
  3. distillation155.2 g of 97.5% pure isopentyl methanephosphonite are distilled out under high vacuum

Sources & evidence

ORD record
ord-b9fad94bddf44f30b901deb6c4a39204
Source dataset
uspto-grants-1986_07
Patent number
US04599207

Reaction notes

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