Potassium Carbonate → HCID 57708764, compound

HRID 219892Notes

Reaction equation

HRID 219892 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 57708764HCID 57708764, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3-cyanophenol (2 000 mg; 16.79 mmol; 1 eq.) was dissolved in DMF (40 mL). Then ethyl 4-bromobutyrate (3 602.35 mg; 18.47 mmol; 1.10 eq.) and K2CO3 (3 480.55 mg; 25.18 mmol; 1.50 eq.) were added to the reaction mixture. The reaction mixture was heated to 80° C. for 2 hours. The reaction mixture was cooled to RT and diluted with EtOAc. The organic layer was washed with water (3×), brine, dried over MgSO4 and concentrated affording the title compound as a colourless liquid (3.92 g, 96%). 1H NMR (DMSO-d6, 300 MHz) δ 7.51-7.38 (m, 3H), 7.29-7.26 (m, 1H), 4.10-4.03 (m, 4H), 2.48-2.43 (t, J=7.37 Hz, 2H), 2.02-1.93 (m, 2H), 1.20-1.15 (t, J=7.10 Hz, 3H). HPLC (Method A) Rt 4.49 min (Purity: 97.9%).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washThe organic layer was washed with water (3×), brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-18c511c3a93b49f08b9fd92621a8bc6e
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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