Hydrochloric Acid → Ethyl 3-(3-cyanophenyl)-3-oxopropanoate

HRID 1062666Notes

Reaction equation

HRID 1062666 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[C:11]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18])(=[O:13])[CH3:12].Cl>O1CCCC1.C(OCC)(=O)C>[C:17]([C:16]1[CH:15]=[C:14]([C:11](=[O:13])[CH2:12][C:3]([O:7][CH2:8][CH3:9])=[O:10])[CH:21]=[CH:20][CH:19]=1)#[N:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 802223-Acetylbenzonitrile

Product 1

HCID 11622629Ethyl 3-(3-cyanophenyl)-3-oxopropanoateYield 96.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of sodium hydride (1.2 g of 60% suspension in mineral oil, hexane-washed, 30.3 mmol) in 40 mL of tetrahydrofuran was added diethyl carbonate (3.7 mL, 30.3 mmol) and 3-acetyl benzonitrile (2.2 g, 15.2 mmol). The resulting suspension was stirred at 65° C. for 1 h and then was cooled to room temperature. There was added 40 mL of 10% aqueous HCl and the reaction mixture was diluted with ethyl acetate and the layers were separated. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to afford 3.2 g (96%) of the title compound, which was sufficiently pure to be used without purification. MS(NH3—CI) 218.3 (M+H)+.

Workup

  1. temperaturewas cooled to room temperature
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d971e61955be4c4488811ecdccd26307
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

Loading…