Methane → HCID 18801070, compound

HRID 1955653Notes

Reaction equation

HRID 1955653 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3([O:23][CH3:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[C:3]=1[NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].O.C>CS(C)=O.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([C:17]3([O:23][CH3:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[C:3]=1[NH:25][C:26](=[O:31])[C:27]([CH3:29])([CH3:28])[CH3:30]

Participants

7

Reactant 3

HCID 297MethaneHCID 962WaterHCID 53718280HCID 53718280, compound

Product 1

HCID 18801070HCID 18801070, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

The product from Example 6 (3.0 g) was dissolved in dimethylsulphoxide and Pd(dba)2 (200 mg) was added. The mixture was treated with H2 at atmospheric pressure until gas uptake ceased. On completion, the reaction was added to water (500 ml) and extracted with ethyl acetate (2×400 ml). The combined organic extracts were washed with water (2×300 ml) and then dried on MgSO4, and filtered. Removal of the solvent in vacuo gave a yellow oil which was dissolved in diethyl ether, treated with charcoal, then filtered through, Hyflo. Removal of the solvent from the filtrate gave the crude title product. Precipitation from ethyl acetate/40°-60° petroleum ether afforded the title product as a white solid; mp 150°-151° C.

Workup

  1. additionThe mixture was treated with H2 at atmospheric pressure until gas uptake
  2. extractionextracted with ethyl acetate (2×400 ml)
  3. washThe combined organic extracts were washed with water (2×300 ml)
  4. customdried on MgSO4
  5. filtrationfiltered
  6. customRemoval of the solvent in vacuo
  7. customgave a yellow oil which
  8. filtrationfiltered through, Hyflo
  9. customRemoval of the solvent from the filtrate
  10. customgave the crude title product
  11. customPrecipitation from ethyl acetate/40°-60° petroleum ether

Sources & evidence

ORD record
ord-ad1316ae28dc465db774c5d8b8a9506b
Source dataset
uspto-grants-1998_07
Patent number
US05776951

Reaction notes

Loading…