Methanol → HCID 66652671, compound

HRID 418928Notes

Reaction equation

HRID 418928 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:9]3[CH2:15][CH2:14][CH2:13][CH:10]32)=C(OS(C(F)(F)F)(=O)=O)[CH:4]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.[C:63]([O:66][CH2:67]C)(=[O:65])[CH3:64]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:67][O:66][C:63]([C:64]1[C:6]2[CH2:7][CH:8]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[CH:9]3[CH2:15][CH2:14][CH2:13][CH:10]3[C:11]=2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:65]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 72309420HCID 72309420, compound

Product 1

HCID 66652671HCID 66652671, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Combine trifluoro-methanesulfonic acid 8-methoxy-4-(4-methoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-6-yl ester (0.1 g, 0.22 mmol), palladium acetate (0.0393 g, 0.18 mmol), 1,3-bis(diphenylphosphino)-propane (0.0723 g, 0.18 mmol), with dDMSO (6 ml) and methanol (2 m), and heat at 80-85° C. for 12 hours under an atmosphere of carbon monoxide. Remove solvent in vacuo, take in ethyl acetate and wash 5× with water. Dry over anhydrous sodium sulfate and chromatograph the residue on silica gel with 10% ethyl acetate in hexanes to yield the titled compound (0.07 g, 88%). 1H NMR (CDCl3): 7.21 (d, J=7.9, Hz, 2H), 7.19 (s, 1H), 6.9(s, 1H), 6.86 (d, J=7.9 Hz, 2H), 3.86 (s, 3H), 3.82 (s, 3H), 3.8 (s, 3H), 3.45 (m, 1H), 3.22 (m, 1H), 3.1 (m, 2H), 2.58 (m, 1H), 2.2 (m, 1H), 1.6-1.3 (m, 5H).

Workup

  1. washwash 5× with water
  2. dry with materialDry over anhydrous sodium sulfate and chromatograph the residue on silica gel with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-65b22253c1a74e8bb0d58d5a3990b711
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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