Reaktion #41964

ord-c72f637ef3974175b04039f65365bb02

Reaktionsgleichung

C[CH2][Mg][Br]
ethyl magnesium bromide
O=C1CCc2cc(F)ccc21
5-fluoroindanone
[Cl-].[NH4+]
ammonium chloride
CCC1(O)CCc2cc(F)ccc21
compound
Ausbeute 93.0%
CCC1(O)CCc2cc(F)ccc21
1-Ethyl-5-fluoro-indan-1-ol
Ausbeute 93.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeQuench
  2. 2
    Sonstigethe reaction
  3. 3
    Waschenwash with water (2×)
  4. 4
    Trocknendry over anhydrous sodium sulfate
  5. 5
    Filtrationfilter
  6. 6
    Einengenconcentrate

Vorschrift

Add ethyl magnesium bromide (1.3 ml, 3.90 mmol, 1.30 equivalents, 3.0 M in tetrahydrofuran) drop wise to a solution of 5-fluoroindanone (450 mg, 3.00 mmol) in. anhydrous ether (5 ml) under nitrogen at room temperature and stir overnight. Quench the reaction by drop wise addition of 10% aqueous ammonium chloride, dilute with ether, wash with water (2×), dry over anhydrous sodium sulfate, filter, and concentrate to obtain the'title compound (502 mg, 93%). NMR (400 MHz, CDCl3): δ 0.94 (t, 3H), 1.79 (m, 1H), 1.92 (m, 1H), 2.12 (m, 1H), 2.31 (m, 1H), 2.81 (m, 1H), 2,98 (m, 1H), 6.91 (m, 2H), 7.24 (m, 1H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728150B2uspto-grants-2010_06