Diethyl Ether → 1-Cyclopropyl-5-fluoroindan-1-ol

HRID 561414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561414
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C(OCC)C.[CH:17]1([Mg]Br)[CH2:19][CH2:18]1>O1CCCC1>[CH:17]1([C:7]2([OH:11])[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)[CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 1365375-Fluoro-1-indanoneHCID 178418630HCID 178418630, Verbindung

Produkt 1

HCID 532567411-Cyclopropyl-5-fluoroindan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2.00 g (13.3 mmol) of 5-fluoro-1-indanone were introduced into 50 ml of diethyl ether at RT, 40 ml (20.0 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were added, and the mixture was stirred at RT overnight. The reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 2.22 g (87% of theory) of the title compound which were reacted without further purification.

Aufarbeitung

  1. additionThe reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-db109bd5a08b4888adb35f8883ee97b8
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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