Acetonitrile → HCID 10831334, compound

HRID 2393587Notes

Reaction equation

HRID 2393587 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1C=C[CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][Cl:25].C(=O)([O-])[O-:27].[K+].[K+].[C:32](#N)[CH3:33]>C(OCC)(=O)C.O>[Cl:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:7](=[O:27])[CH:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][CH3:10])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentaneHCID 18976459HCID 18976459, compound

Product 1

HCID 10831334HCID 10831334, compound

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

A solution of 2.31 g (9.6 mmol) of 4-hydroxy-2'-phenylbutyrophenone and 1.56 ml (12.0 mmol) of 1-bromo-5-chloropentane in 200 ml of acetonitrile is mixed with 1.59 g (11.5 mmol) of potassium carbonate, and it is refluxed overnight (16 hours). For working-up,-the reaction mixture is taken up in ethyl acetate/water, the organic phase is washed with water and dried on sodium sulfate. After the drying agent is filtered off and after concentration by evaporation, the crude product is chromatographed on silica gel (hexane/ethyl acetate, gradient to 95:5), yield 2.79 g (84%) as oil.

Workup

  1. temperatureis refluxed overnight (16 hours)
  2. washthe organic phase is washed with water
  3. customdried on sodium sulfate
  4. filtrationAfter the drying agent is filtered off
  5. concentrationafter concentration
  6. customby evaporation
  7. customthe crude product is chromatographed on silica gel (hexane/ethyl acetate, gradient to 95:5), yield 2.79 g (84%) as oil

Sources & evidence

ORD record
ord-050ce2c8039746a3a46b138379bbfd74
Source dataset
uspto-grants-1998_09
Patent number
US05807899

Reaction notes

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