Hydrochloric Acid → Ethyl 2-(4-benzyloxyphenyl)cyanoacetate

HRID 398026

Reaction equation

HRID 398026 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][C:14]#[N:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+].[C:22](=O)([O:26]CC)[O:23][CH2:24][CH3:25].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]([C:14]#[N:15])[C:22]([O:23][CH2:24][CH3:25])=[O:26])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 5228044-BenzyloxyphenylacetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 23001570Ethyl 2-(4-benzyloxyphenyl)cyanoacetateYield 99.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 4-benzyloxybenzyl cyanide from step (450a)(3.2 g, 14.33 mmol), sodium ethoxide (1.07 g, 15.7 mmol), and diethyl carbonate (2.23 g, 18.9 mmol) were combined in toluene (100 mL), heated to reflux for 3 h, cooled to rt, and partioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude was purified by chromatography on silica gel eluting hexane:ethyl acetate (80:20, v:v) to give ethyl 2-(4-benzyloxyphenyl)cyanoacetate (4.2 g, 99%) as an oil. MS (M+NH4)+=313.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by chromatography on silica gel
  7. washeluting hexane:ethyl acetate (80:20, v:v)

Sources & evidence

ORD record
ord-94741de82d734d9693cabe305f6d8d9d
Source dataset
uspto-grants-2003_08
Patent number
US06610731B2

Linked notes

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