Dimethyl Sulfoxide → HCID 67158730, compound

HRID 550203Notes

Reaction equation

HRID 550203 reaction equation
[CH2:1]([C:3]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH:10]=[CH:9]2)=[CH:4][CH3:5])[CH3:2].CCN(CC)CC.CS(C)=O.[C]=[O:36].C[CH2:38][O:39][CH2:40]C>CO.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:38][O:39][C:40]([C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([C:3]([CH2:1][CH3:2])=[CH:4][CH3:5])[CH:7]=2)[CH:12]=1)=[O:36]

Participants

9

Reactant 5

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 76647763HCID 76647763, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 67158730HCID 67158730, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 887MethanolSolvent

Procedure

Treat a mixture containing trifluoromethanesulfonic acid 6-(1-ethylpropenyl)naphthalen-2-yl ester (0.92 g, 2.67 mmol), Pd(OAc)2 (0.020 mg, 0.09 mmol), bis-(diphenylphosphino)ferrocene (0.046 g, 0.083 mmol), Et3N (0.67 mL, 4.81 mmol), in MeOH (10 mL) and DMSO (15 mL) with carbon monoxide at 100 psi at 80° C. for 4 h. Pour the reaction mixture into ether (100 mL) and wash the mixture with brine (4×50 mL). Dilute the organic layer with EtOAc (100 mL), wash with brine, then dry over Na2SO4 and filter. Concentrate the filtrate to give the title compound as an off-white solid (0.67 g, quant). MS (ES) in/e 255 (M+1).

Workup

  1. additionTreat a mixture
  2. washwash the mixture with brine (4×50 mL)
  3. additionDilute the organic layer with EtOAc (100 mL)
  4. washwash with brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-c1eaff9626344ac1aad21f1c0eedc939
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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