Reaktion #2303913

Reaktionsgleichung

water

5-methyl-2,3-diphenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-4-one

LiAlH4

water

→

5-methyl-2,3-diphenyl-5,6-dihydro-4H-cyclopenta[b]thiophen -4-ol

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwas extracted with ether (3×50 mL)
2. 2
   WaschenThe combined organic layers were washed with water
3. 3
   Trocknendried over MgSO4
4. 4
   Sonstigeevaporated off to dryness

Vorschrift

A solution of 5-methyl-2,3-diphenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-4-one (6.08 g, 20 mmol) in 75 mL of ether was slowly added to a solution of LiAlH4 (0.38 g, 10 mmol) in 50 mL of ether and stirred overnight. The resulting suspension was poured into a mixture of ice and water, the organic layer was isolated, while the water layer was extracted with ether (3×50 mL). The combined organic layers were washed with water, dried over MgSO4 and evaporated off to dryness. The 5-methyl-2,3-diphenyl-5,6-dihydro-4H-cyclopenta[b]thiophen -4-ol so obtained was dissolved in 100 mL of benzene, added of 1 g of p-toluenesulfonic acid and was refluxed for 10 min. Then the reaction mixture was cooled to room temperature and treated with a saturated aqueous solution of Na2CO3. The organic phase was isolated, dried over MgSO4 and evaporated off to dryness giving the crystallized product. Yield 3.46 g (60% with respect to the starting ketone).

Quelle