反応 #1148664

反応方程式

2-indanone

phenylmagnesium bromide

HCl

water

→

crystals

収率 64.3%

2-Phenylindene

収率 64.3%

溶媒

benzene

benzene

—

hexanes

反応条件

後処理

1. 1
   温度The solution was cooled to 0° C.
2. 2
   洗浄washed with brine (2×100 mL)
3. 3
   抽出The aqueous layer was extracted with hexanes (2×50 mL)
4. 4
   乾燥the combined organic layers were dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   その他the solvent removed in vacuo from the filtrate
7. 7
   その他to yield a brown oil
8. 8
   workup.ADDITIONcontaining 4 Å molecular sieves
9. 9
   温度After refluxing for 2.5 hours
10. 10
    ろ過the solution was filtered
11. 11
    温度cooled to 5° C. overnight
12. 12
    ろ過The product, a white flaky solid, was collected by filtration
13. 13
    洗浄was washed with 50 mL of cold benzene
14. 14
    その他Additional product is obtained
15. 15
    濃縮by concentrating the filtrate
16. 16
    温度cooling

実験手順

A solution of 2-indanone (13.47 g, 102 mmol) in anhydrous benzene (100 mL) was added to phenylmagnesium bromide (3.0 M in diethyl ether, 50.9 mL. 153 mmol) at 5° C. over 2.5 hours. The reaction was allowed to warm to room temperature over 30 minutes. The solution was cooled to 0° C. and 150 mL of water are added. The resultant mixture was diluted with 200 mL of hexanes, neutralized with 5 M HCl, and washed with brine (2×100 mL). The aqueous layer was extracted with hexanes (2×50 mL), and the combined organic layers were dried (MgSO4), filtered, and the solvent removed in vacuo from the filtrate to yield a brown oil. This oil and p-toluenesulfonic acid (0.50 g) were dissolved in benzene (250 mL) in a round-bottom flask below a Soxhlet extractor containing 4 Å molecular sieves. After refluxing for 2.5 hours, the solution was filtered and cooled to 5° C. overnight. The product, a white flaky solid, was collected by filtration, and was washed with 50 mL of cold benzene. Additional product is obtained by concentrating the filtrate, cooling, and filtering the crystals (12.60 g, 64.3% yield). 1H NMR (400 MHz, 20 C, CDCl3) 7.62 (d, J=7.3 Hz, 2H), 7.47 (d, J=7.3 Hz, 1H), 7.39 (M, 3H), 7.27 (m, 2H), 7.22 (s, 1H), 7.18(t, J=7.4 Hz, 1H), 3.78(S<2H), 13C{1H} NMR (100 MHz, 20 C, CDCl3): 146.3, 145.3, 143.1, 135.9, 128.6, 127.5, 126.5, 126.4, 125.6, 124.7, 123.6, 120.9, 38.9.

出典