Реакция #652144

Уравнение реакции

2-indanone

toluene

Toluene

→

indanol

Условия реакции

Обработка

1. 1
   Фильтрацияfiltered over a plug of Celite
2. 2
   Другоеevacuated
3. 3
   Другоеto yield a brown oil
4. 4
   workup.ADDITIONwas added dropwise
5. 5
   Другоеto give a tan-brown slurry
6. 6
   ТемператураThis mixture was warmed to room temperature
7. 7
   ТемператураAfter cooling to 0° C. it
8. 8
   Другоеwas quenched with 150 mL of water, hexane (200 mL)
9. 9
   workup.ADDITIONadded
10. 10
    ДругоеThe organic layer was separated
11. 11
    Экстракцияthe aqueous layer was extracted with two 50-mL portions of hexane
12. 12
    ПромывкаThe combined organic layers were washed with two 50-mL portions of brine
13. 13
    Сушкаdried over anhydrous magnesium sulfate
14. 14
    ФильтрацияAfter filtration over Celite
15. 15
    Другоеthe solvent was removed under vacuo

Методика

A 3-neck 500 mL round-bottomed flask fitted with a condenser and an addition funnel was charged with 2.62 g (0.11 mol) of Mg turnings and 20 mL of anhydrous diethyl ether. Slow addition of a solution of 25.10 g (0.09 mol) of 3,5-bis(trifluoromethyl) bromobenzene in diethyl ether (100 mL), followed by refluxing for 30 min, gave a brown-grey solution of the aryl Grignard reagent. The solution was cooled to room temperature (RT), filtered over a plug of Celite and evacuated to yield a brown oil. Toluene (40 mL) was added and the suspension cooled to 0° C. whereupon a solution of 2-indanone (9.22 g, 0.07 mol) in toluene (60 mL) was added dropwise to give a tan-brown slurry. This mixture was warmed to room temperature and stirred for an additional 3 hours. After cooling to 0° C. it was quenched with 150 mL of water, hexane (200 mL) added and the reaction mixture neutralized with 5M HCl. The organic layer was separated, and the aqueous layer was extracted with two 50-mL portions of hexane. The combined organic layers were washed with two 50-mL portions of brine and dried over anhydrous magnesium sulfate. After filtration over Celite, the solvent was removed under vacuo yielding 21.5 g (89% based on 2-indanone) of 2-(bis-3,5-trifluoromethylphenyl) indanol as an off-white solid. 1H NMR (CDCl3, 23 C., 400 MHz): d 8.05 (s, 2H), 7.80 (s, 1H), 7.5-7.0 (M, 4H), 3.41 (m, 4H), 2.21 (s, 1H, OH). Under argon, this alcohol (21.5 g, 0.06 mol) and p-toluene-sulfonic acid monohydrate (800 mg) were dissolved in toluene (250 mL) and the solution was heated to reflux for 6 hours to afford 14.4 g, (70%) of 2-(bis-3,5-(trifluoromethyl)-phenyl)indene upon recrystallization from diethyl ether/hexane at −18 C. 1H NMR (CDCl3, 23° C., 400 MHz): d 8.01 (s, 2H), Arf), 7.75 (s, 1H, Arf), 7.52 (d, J=7 Hz, 1H), 7.47 (d, J=7 Hz, 1H), 7.43 (s, 1H), 7.33 (dd, 2J=7 Hz, 1H), 7.27 (dd, 2J=7 Hz, 1H), 2.83 (s, 2H). 13C NMR (CDCl3, 23 C., 100 MHz): L144.3 (s), 143.1 (s), 138.0 (s), 132.1 (q,2JC-F=33 Hz), 130.1 (d, JC-H=167 Hz), 127.0 (dd), JC-H=160 Hz, 2JC-H=7 Hz), 126.0 (dd, JC-H=159 Hz, 2JC-H=7 Hz)m 125.2 (brd, JC-H=162 Hz), 123.9 (dd, JC-H=156 Hz, 2JC-H=9 Hz), 123.4 (q, JC-F=273 Hz, CF3), 121.8 (dd, Jc-H=160 Hz, 2JC-H=8 Hz), 120.6 (brd, JC-H=167 Hz), 38.9 (td, JC-H=127 Hz, 2JC-H=7 Hz, CH2). C,H analysis: Anal. Found (Calcd): C, 62.45 (62-20); H, 3.01 (3.07).

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