Water → Ethyl 3-(4-cyano-3-methoxyphenyl)oxirane-2-carboxylate

HRID 1519573Notes

Reaction equation

HRID 1519573 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH3:12])[CH:4]=1)=[O:2].[CH2:13]([O:15][C:16](=[O:19])[CH2:17]Cl)[CH3:14].CC[O-].[Na+].O>C1C=CC=CC=1.C(O)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[O:2][CH:17]2[C:16]([O:15][CH2:13][CH3:14])=[O:19])=[CH:4][C:5]=1[O:11][CH3:12])#[N:8]

Participants

7

Reactant 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 2723922Sodium ethoxideHCID 600485344-Formyl-2-methoxybenzonitrile

Product 1

HCID 86694471Ethyl 3-(4-cyano-3-methoxyphenyl)oxirane-2-carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A mixture of 4-formyl-2-methoxybenzonitrile (383 mg, 2.38 mmol) and chloroacetic acid ethyl ester (291 mg, 2.38 mmol) were dissolved in 10 mL of dry benzene. Freshly prepared EtONa (3.09 mmol) in 2.5 mL of ethanol was added, and the mixture were stirred at room temperature for 2 hours. The mixture was added water, then extracted with EtOAc. The organic layers were dried over Na2SO4 and concentrated to afford ethyl 3-(4-cyano-3-methoxyphenyl)oxirane-2-carboxylate. MS m/z: 248 (M+1)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6c84f276db3e44a0a421c23da3162514
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…