[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:19]=[O:20])=[C:6]([NH:8][C:9](=[O:18])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1.[F:21][C:22]([SiH3])([F:24])[F:23].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>CCOCC.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:19]([OH:20])[C:22]([F:24])([F:23])[F:21])=[C:6]([NH:8][C:9](=[O:18])[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=1
To a mixture of aldehyde from Step 3 (252 mg, 0.929 mmol) and THF (8 mL) under argon at 0° C., was added trifluoromethylsilane (132 mg, 0.929 mmol), followed by tetrabutylammonium fluoride (1M solution in THF, 50 mL). The reaction was warmed to 23° C. After 2 h at 23° C., the reaction was treated with 3N HCl (125 mL). After 4 h, the reaction was diluted with ether (75 mL), washed with brine (2×100 mL), and dried (MgSO4). Concentration in vacuo afforded a brown oil (214 mg, 67.4%) which was taken on to the next step without further purification: 1H NMR (CDCl3) δ2.63 (t, J=7 Hz), 2.97 (t, J=7 Hz), 4.68 (br s), 4.88 (q, J=6 Hz), 6.73-6.82 (m), 7.11-7.35 (m), 7.83-7.92 (m), 8.85 (br s). IR (neat) 3450-3050, 1667 cm−1. MS (EI) 341 (M+), 323, 209, 140. Anal. Calc'd. for C17H15NO2F4: C, 59.82; H, 4.43; N, 4.10. Found: C, 59.81; H, 4.57; N, 4.08.
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