Ethyl Acetate → HCID 19703235, compound

HRID 861403Notes

Reaction equation

HRID 861403 reaction equation
[C:1]1([C:7]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH2:9][CH2:10][C:11]([NH2:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CS(O)(=O)=O>[C:1]1([C:7]2([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 54280630HCID 54280630, compound

Product 1

HCID 19703235HCID 19703235, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

5,6-Diphenyl-4-hexenamide (30 g) from step (d) was added to a stirred solution of phosphorous pentoxide (25 g) in methanesulfonic acid (250 mL) at 100°-110° C. The reaction was stirred for several minutes; then the reaction mixture was poured slowly into an ice-cooled mixture of saturated aqueous sodium bicarbonate and ethyl acetate. The mixture was extracted with ethyl acetate and the ethyl acetate layer was separated, washed with aq. NaHCO3, water and brine and dried (MgSO4). Concentration of the solvent to dryness afforded the crude amide which was purified by chromatography on silica gel and elution with 75% ethyl acetate: hexane to give the title compound as a solid (16.5 g).

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe ethyl acetate layer was separated
  4. washwashed with aq. NaHCO3, water and brine
  5. dry with materialdried (MgSO4)
  6. customConcentration of the solvent to dryness afforded the crude amide which
  7. customwas purified by chromatography on silica gel and elution with 75% ethyl acetate

Sources & evidence

ORD record
ord-3a2f78cec92546dcb90dc818ccfe3e83
Source dataset
uspto-grants-1998_02
Patent number
US05714500

Reaction notes

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