반응 #1007291

반응 방정식

product

6-(Benzyloxy)-2,3-dihydroinden-1-one

NaBH4

→

title compound

수율 72.0%

6-(Benzyloxy)-2,3-dihydro-1H-inden-1-ol

수율 72.0%

용매

MeOH

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated
2. 2
   workup.ADDITIONcharged with 200 mL of aqueous NaOH (20%)
3. 3
   추출The resulted mixture was extracted with EtOAc (200 mL×3)
4. 4
   세척The combined organic extracts was washed with brine (200 mL×3)
5. 5
   기타dried
6. 6
   농축concentrated

실험 절차

To a stirred solution of the product from Step A (44 g, 0.185 mol) in 500 mL of MeOH was added NaBH4 (7.1 g, 0.186 mol) in portions at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 20 hours. The reaction mixture was concentrated and charged with 200 mL of aqueous NaOH (20%). The resulted mixture was extracted with EtOAc (200 mL×3). The combined organic extracts was washed with brine (200 mL×3), dried, and concentrated to give the title compound (32.0 g, 72%) as a white solid. 1H-NMR (600 MHz, CDCl3) δ 7.46-7.42 (m, 2H), 7.41-7.36 (m, 2H), 7.34-7.30 (m, 1H), 7.15 (d, J=8.2 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.90 (dd, J=8.2, 2.5 Hz, 1H), 5.20 (t, J=6.2 Hz, 1H), 5.07 (s, 2H), 3.01-2.95 (m, 1H), 2.79-2.72 (m, 1H), 2.55-2.47 (m, 1H), 2.01-1.87 (m, 1H) ppm.

출처