Water → HCID 20333863, compound

HRID 2051618Notes

Reaction equation

HRID 2051618 reaction equation
[H-].[Na+].[C:3]([O:8][CH2:9][CH3:10])(=O)[CH:4]([CH3:6])O.[C:11](#[N:14])C=C.[OH2:15]>O1CCCC1>[C:11]([CH:4]1[CH2:3][O:8][CH:9]([CH3:10])[C:6]1=[O:15])#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7344Ethyl LactateHCID 7855AcrylonitrileHCID 24758Sodium hydride

Product 1

HCID 20333863HCID 20333863, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.7 g (0.2 mol) of sodium hydride are suspended in 100 ml of tetrahydrofuran and the suspension is stirred at room temperature for 90 minutes with 23.6 g (0.2 mol) of ethyl lactate. 9.5 g (0.18 mol) of acrylonitrile are then added dropwise at 60° C. and the mixture is refluxed for 90 minutes. The mixture is poured into 200 ml of water and washed twice with 100 ml of ether each time. The aqueous phase is adjusted to pH 1 with 2-N hydrochloric acid and extracted three times with 150 ml of ether each time. The dried and concentrated ether phases give 20.1 g (89%) of 4-cyano-2-methyltetrahydrofuran-3-one of boiling point 116°-118° C./14 mmHg; IR: 2250 (CN), 1780 (C=O); NMR (CDCl3): 1.37 ppm doublet (CH3); 3.4-4.9 ppm multiplet.

Workup

  1. temperaturethe mixture is refluxed for 90 minutes
  2. washwashed twice with 100 ml of ether each time
  3. extractionextracted three times with 150 ml of ether each time
  4. customThe dried

Sources & evidence

ORD record
ord-c969039556424797b231c7d2d3cdc501
Source dataset
uspto-grants-1980_01
Patent number
US04181666

Reaction notes

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