Sodium borohydride → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-ol

反応式

[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9](=[O:14])[CH2:8][CH2:7]2>C(O)C.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([OH:14])[CH2:8][CH2:7]2

参加物

実験手順

Sodium borohydride (1.67 g) was added in portions to a solution of 6-fluoro-2-tetralone (6.56 g) in dry ethanol (30 ml) with stirring, keeping the temperature below 25° C. The mixture was then stirred at room temperature for 3 hours. The mixture was then diluted with a little ethyl acetate and concentrated to an oily residue. Dilute sulphuric acid was added dropwise until effervescence no longer occurred. The mixture was extracted with ether and the extract washed, dried, and concentrated to give an oil. This was distilled (b.p. 75-77/0.1 Torr) to give 6-fluorotetralin-2-ol (5.31 g) containing a trace of the tetralone starting material.