Reaktion #41969

Reaktionsgleichung

ammonium chloride

5-fluoroindanone

cyclopropyl magnesium bromide

→

title compound

Ausbeute 106.8%

1-Cyclopropyl-5-fluoro-indan-1-ol

Ausbeute 106.8%

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile maintaining a gentle reflux
2. 2
   Sonstigequench
3. 3
   Sonstigethe reaction at room temperature
4. 4
   workup.ADDITIONDilute
5. 5
   Waschenwash with water (2×)
6. 6
   Trocknendry over anhydrous sodium sulfate
7. 7
   Filtrationfilter
8. 8
   Einengenconcentrate

Vorschrift

To a solution of 5-fluoroindanone (0.95 g, 6.33 mmol) in anhydrous ether (30 ml) under nitrogen at room temperature add cyclopropyl magnesium bromide (9.1 ml, 7.28 mmol, 1.15 equivalents, 0.80 M in tetrahydrofuran) dropwise while maintaining a gentle reflux. After stirring overnight, quench the reaction at room temperature via dropwise addition of 10% aqueous ammonium chloride. Dilute the reaction with ether, wash with water (2×), dry over anhydrous sodium sulfate, filter, and concentrate to give the title compound (1.30 g, ˜100%). NMR (CDCl3, 400 MHz): δ 0.26 (m, 1H), 0.36-0.51 (m, 3H), 1.21 (m, 1H), 2.13 (m, 1H), 2.28 (m, 1H), 2.80 (m, 1H), 2.95 (m, 1H), 6.88 (m, 2H), 7.29 (m, 1H).

Quelle