5-Chloro-1-indanone → 5-Chloro-2,3-dihydro-1H-inden-1-ol

Temperature

10 °C

To a precooled (5–10° C.) solution of 5-chloro-indan-1-one (2.0 g, 12 mmoles) in 33 mL of anhydrous methanol was added sodium borohydride (0.43 g, 11 mmoles). The reaction mixture was stirred at 10° C. for 2 hrs and then at room temperature for 18 hrs. The reaction mixture was evaporated to afford a yellow residue. The residue was dissolved in 200 mL of diethyl ether and then washed with water (2×100 mL), with 0.10 N hydrochloric acid (2×100 mL), and then with brine (100 mL). The organic layer was separated, dried (sodium sulfate), filtered, and the filtrate was evaporated to provide the title compound in good purity. MS m/z 167 (M−1).

1. waitat room temperature for 18 hrs
2. customThe reaction mixture was evaporated
3. customto afford a yellow residue
4. washwashed with water (2×100 mL), with 0.10 N hydrochloric acid (2×100 mL)
5. customThe organic layer was separated
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. customthe filtrate was evaporated

ORD record

ord-6f126b94db9f44529457729dac328bc6

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07244763B2