Diethyl Carbonate → Ethyl 2-(4-benzyloxyphenyl)cyanoacetate

HRID 1106656Notes

Reaction equation

HRID 1106656 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]>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 5228044-BenzyloxyphenylacetonitrileHCID 2723922Sodium ethoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 partitioned 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. custompartitioned between ethyl acetate and 1 N HCl
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by chromatography on silica gel
  8. washeluting hexane: ethyl acetate (80:20, v:v)

Sources & evidence

ORD record
ord-cfecfa198e244158a2645819786085c1
Source dataset
uspto-grants-2000_05
Patent number
US06057336

Reaction notes

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