Water → HCID 12052996, compound
Reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH2:7][CH:8]([CH3:11])[C:9](=[O:10])[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC>[CH3:1][C:2]1[S:6][C:5]2[CH2:7][CH:8]([CH3:11])[CH:9]([OH:10])[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2,5-dimethyl-3-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-4-one (4.4 g, 18 mmol) in 50 mL of ether was slowly added to a solution of LiAlH4 (0.35 g, 9 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 2,5-dimethyl-3-phenyl-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. The residue was passed through a column packed with Al2O3 by using hexane as eluent. The evaporation of the yellow fraction was given the crystallized product. Yield 1.5 g (37% based on the starting ketone).
Workup
- extractionwas extracted with ether (3×50 mL)
- washThe combined organic layers were washed with water
- dry with materialdried over MgSO4
- customevaporated off to dryness
Sources & evidence
- ORD record
- ord-dd94e4b6061f41e79fca4e02b05ac2f2
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07112638B2
Reaction notes
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