trans-(4-(trifluoromethyl)cyclohexyl)methanol synthesis

Yield:1202577-61-4 100%

Reaction Conditions:

with borane-THF in tetrahydrofuran at 0 - 20; for 2 h;

Steps:

32 Reference Example 32: Synthesis of trans-4-(trifluoromethyl)cyclohexyl)methanol
trans-4-(Trifluoromethyl)cyclohexane-1-carboxylic acid (0.400 g, 2.04 mmol) was dissolved in THF (5.1 mL) and a solution of borane-THF complex in THF (0.90 M, 2.72 mL, 2.45 mmol) was added at 0° C.
After stirring the reaction mixture at room temperature for 2 hours, distilled water was added to the reaction mixture, the aqueous layer was extracted with ethyl acetate.
The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure to obtain the title compound (hereinafter referred to as the compound of Reference Example 32) (0.370 g, 2.04 mmol, quantitative) as a colorless oil.
¹H-NMR (400 MHz, CDCl₃) δ: 0.94-1.05 (m, 2H), 1.26-1.38 (m, 3H), 1.43-1.53 (m, 1H), 1.91-2.02 (m, 5H), 3.49 (t, J=5.7 Hz, 2H).

References:

Toray Industries, Inc.;Osumi, Kazuya;Matsumura, Yuki;Hayashi, Shinnosuke;Hoshi, Masaki;Vallet, Martial;Yokosaka, Shinya;Aoki, Takumi;Meguro, Hiroyuki;Kaino, Mie;Takagaki, Kozuc;Sasaki, Rie US2020/392107, 2020, A1 Location in patent:Paragraph 0423-0425

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