Reaktion #698652

Reaktionsgleichung

water

lithium aluminum hydride

ketopinic acid

→

white powder

7,7-Dimethyl-2-hydroxy-1-hydroxymethyl bicyclo[2.2.1]heptane

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Sonstigethe ice bath was removed
4. 4
   TemperaturThe mixture was cooled again
5. 5
   workup.ADDITIONwet ether was added cautiously
6. 6
   SonstigeWhen the violent reaction
7. 7
   ExtraktionThe mixture was then extracted three times with ethyl acetate
8. 8
   WaschenThe combined extracts were washed with water and brine
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    SonstigeEvaporation of the solution

Vorschrift

To an ice-cooled mixture of lithium aluminum hydride (4 g, 105.4 mmol) in ether was added dropwise a solution of camphorsulfonyl chloride (10 g, 39.88 mmol) and ketopinic acid, prepared as described in Step 1, above. After the addition was complete, the ice bath was removed and the mixture was stirred at ambient temperature for 2 hrs. The mixture was cooled again and wet ether was added cautiously. When the violent reaction subsided, water was added. The mixture was then extracted three times with ethyl acetate. The combined extracts were washed with water and brine and dried over anhydrous magnesium sulfate. Evaporation of the solution gave 4.8 g of a white powder. NMR(δ): 0.90 (s, 3H), 1.20 (s, 3H).

Quelle