Trifluoroacetic acid → 4-(Adamantan-2-yl)-3-chlorobenzoic acid

反応式

[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[C:15]1(O)[CH:22]2[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:24][CH:16]1[CH2:17]3)[CH2:21]2)[C:5]([O:7]C(C)(C)C)=[O:6].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH:16]12[CH2:24][CH:20]3[CH2:19][CH:18]([CH2:23][CH:22]([CH2:21]3)[CH:15]1[C:14]1[CH:13]=[CH:12][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[Cl:1])[CH2:17]2

参加物

実験手順

To a solution of tert-butyl 3-chloro-4-(2-hydroxyadamantan-2-yl)benzoate (0.581 g, 1.60 mmol) in dichloromethane (50 mL) was added triethylsilane (5 mL) and trifluoroacetic acid (5 mL). The reaction mixture was stirred at ambient temperature for 20 hours and the reaction solution was concentrated in vacuo to dryness. The residue was triturated with hexanes (15 mL) to afford the title compound (0.27 g, 57%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.06 (d, J=1.6 Hz, 1H), 7.94 (dd, J=1.6, 8.2 Hz, 1H), 7.70 (d, J=8.2 Hz, 1H), 3.33 (s, 1H), 2.33 (br s, 2H), 1.98-1.92 (m, 8H), 1.78 (s, 2H), 1.70-1.66 (m, 2H) (OH not observed); MS (ES−) m/z 289.3, 291.3 (M−1).