Reaktion #1079978

Reaktionsgleichung

tetrahydrofuran

HCl

diethyl ether

LiAlH4

tetrahydrofuran

Adamantylfulvene

→

product

2-adamantylcyclopentadiene

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 500 mL argon-purged round bottom flask
2. 2
   Temperaturthe reaction was cooled to 0° C.
3. 3
   SonstigeThe organic later was isolated
4. 4
   Extraktionthe aqueous layer extracted with diethyl ether (3×50 mL)
5. 5
   TrocknenThe combined organic layers were dried over MgSO4
6. 6
   Filtrationfiltered

Vorschrift

A 500 mL argon-purged round bottom flask was charged with LiAlH4 (8.20 g, 216 mmol) and 100 mL tetrahydrofuran. Adamantylfulvene (30.00 g, 151.3 mmol) was added via solid addition funnel, followed by another 100 mL tetrahydrofuran over 2 minutes at 0° C. After stirring for 22 hours at room temperature, the reaction was cooled to 0° C. and 100 mL water were added dropwise over 60 minutes. Then, 100 mL concentrated aqueous HCl in 300 mL water and 50 mL diethyl ether were added. The organic later was isolated and the aqueous layer extracted with diethyl ether (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and rotavapped to give 30.30 g of product in quantitative yield.

Quelle