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A mixture of ethyl (±)-10,11-dihydro-3-(trifluoromethanesulfonyioxy)-5H-dibenzo[a,d]cycloheptene-10-acetate (808.9 mg, 1.89 mmol), KOAc (742 mg, 7.56 mmol), Pd(OAc)2 (21.2 mg, 0.095 mmol), 1,1'-bis(diphenylphosphino)ferrocene (210 mg, 0.38 mmol), and anhydrous DMSO (11 mL) was purged with carbon monoxide (three evacuation/CO flush cycles, followed by bubbling CO through the mixture for 5 min), then was stirred under a balloon of CO in an oil bath set at 70° C. After 3.5 h, the reaction was diluted with H2O (11 mL), cooled to 0° C., and acidified with 1.0 N HCl (ca. 8 mL). CH2Cl2 extraction (3×30 mL), drying (Na2SO4), concentration, and reconcentration from toluene left a reddish-orange liquid (2-3 mL). Chromatography (silica gel, 3:2:0.1 EtOAc/toluene/AcOH; mixed fractions again with 1:1:0.1 EtOAc/toluene/AcOH) gave the title compound (581.9 mg, 95%) as a viscous, yellow oil which partially crystallized in high vacuum at 40° C: TLC Rf (3:2:0.1 EtOAc/toluene/AcOH) 0.60; 1H NMR (250 MHz, CDCl3) δ 7.95 (d, J=1.5 Hz, 1H), 7.87 (dd, J=7.8, 1.5 Hz, 1H), 7.00-7.35 (m, 5H), 4.40 (d, J=15.2 Hz, 1H), 4.19 (q, J=7.1 Hz, 2H), 3.97 (d, J=15.2 Hz, 1H), 3.82-4.00 (m, 1H), 3.43 (dd, J=15.3, 4.0 Hz, 1H), 3.07 (dd, J=15.3, 9.5 Hz, 1H), 2.69 (dd, J=15.8, 4.8 Hz, 1H), 2.53 (dd, J=15.8, 9.5 Hz, 1H), 1.28 (t, J=7.1 Hz, 3H); FTIR (CCl4) 2357-337 (broad), 1735, 1692, 1280 cm-1 ; MS (ES) m/e 342.2 (M+NH4)+, 325.2 (M+H)+, 307.2 (M+H-H2O)+.

1. customwas purged with carbon monoxide (three evacuation/CO
2. customflush cycles
3. customby bubbling CO through the mixture for 5 min),
4. customset at 70° C
5. additionthe reaction was diluted with H2O (11 mL)
6. extractionCH2Cl2 extraction (3×30 mL)
7. customdrying
8. concentration(Na2SO4), concentration, and reconcentration from toluene
9. waitleft a reddish-orange liquid (2-3 mL)