Ethanol → HCID 55267882, compound

HRID 869004Notes

Reaction equation

HRID 869004 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])#[N:2].[CH2:9]([OH:11])[CH3:10].C([O-])([O-])=O.[K+].[K+]>CCCCCC.O.[Cl-].[Na+].O>[CH2:9]([O:11][C:1](=[NH:2])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH3:10]

Participants

7

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 77749Propanoic acid, 3-cyano-, methyl ester

Product 1

HCID 55267882HCID 55267882, compoundYield 63.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8058HexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of methyl 3-cyanopropanoate (1.5 g, 13.3 mmol) and ethanol (0.61 g, 13.3 mmol) in n-hexane (15 mL) was cooled to −30° C., and anhydrous hydrogen chloride was bubbled into the solution for 1 h. The mixture was allowed to stand overnight at about −15° C., then at 5-10° C. for 16 h. The solvent was decanted, and the residue was diluted with diethyl ether (30 mL×2) and a solution of K2CO3 (3.67 g, 26.6 mmol) in water (25 mL), the organic layer was washed with water (20 mL) and brine (10 mL), dried, and concentrated to give a colorless oil (1.34 g). MS (ESI): m/z 160 [M+H]+.

Workup

  1. customanhydrous hydrogen chloride was bubbled into the solution for 1 h
  2. waitat 5-10° C. for 16 h
  3. customThe solvent was decanted
  4. additionthe residue was diluted with diethyl ether (30 mL×2)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-de31a547df554c9783373f4d1befb338
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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