Acetic Anhydride → 2-Methylpropyl 2-cyano-3-ethoxyprop-2-enoate

HRID 1980219Notes

Reaction equation

HRID 1980219 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5])#[N:2].[C:11]([O:14][C:15](=O)C)(=O)[CH3:12].C(OCC)(OCC)OCC>>[C:1]([C:3](=[CH:15][O:14][CH2:11][CH3:12])[C:4]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5])#[N:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 25918Acetic acid, cyano-, 2-methylpropyl esterHCID 31214Ethyl orthoformate

Product 1

HCID 537568292-Methylpropyl 2-cyano-3-ethoxyprop-2-enoate

Procedure

A mixture of isobutyl cyanoacetate (30 g), acetic anhydride (58 ml) and triethyl orthoformate (43 ml) was heated under reflux for 6 hours. The volatile material was evaporated and the residue was distilled to give isobutyl 2-cyano-3-ethoxy-2-propenoate, b.p. 130°-133° C./0.4 mm. A solution of this (6 g) in ethanol (30 ml) was mixed with benzylmethylamine (4 ml). The mixture was heated under reflux for 10 minutes and then cooled and diluted with water (50 ml). The solid was filtered and recrystallised from ethanol giving isobutyl 3-(benzylmethylamino)-2-cyano-2-propenoate, mp 105°-106° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe volatile material was evaporated
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-55405d428a034e609ccfb9bd77590936
Source dataset
uspto-grants-1985_04
Patent number
US04508659

Reaction notes

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