Dimethylformamide → 8-[(E)-2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one

HRID 2275297Notes

Reaction equation

CN(C=O)C.[CH3:6][C:7]1([CH3:33])[C:19]2[O:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[C:15]=2[C:14](=[O:24])[C:13]2[C:8]1=[CH:9][C:10](OS(C(F)(F)F)(=O)=O)=[CH:11][CH:12]=2.[CH3:34][C:35]1([CH3:42])[O:39][CH:38]([CH:40]=[CH2:41])[CH2:37][O:36]1.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:34][C:35]1([CH3:42])[O:39][CH:38](/[CH:40]=[CH:41]/[C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[C:14](=[O:24])[C:15]2[C:16]4[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=4[O:18][C:19]=2[C:7]3([CH3:33])[CH3:6])[CH2:37][O:36]1

Participants

Conditions

Temperature: 100 °C

Procedure

To the DMF solution (4 ml) of trifluoro-methanesulfonic acid 6,6-dimethyl-11-oxo-6,11-dihydro-benzo[b]naphtho[2,3-d]furan-8-yl ester (300 mg), 2,2-dimethyl-4-vinyl-[1,3]dioxolane (469 mg) and PdCl2(PPh3)2 (103 mg), sodium hydrocarbonate (184 mg) was added, and the mixture was stirred at 100° C. overnight under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (130 mg, 46%).

Workup

washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
concentrationconcentrated under reduced pressure
customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-fdc27b0a9ff14e5d9419ac1073b02862
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126931B2

Reaction notes

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