Water → HCID 67174670, compound

HRID 2216731Notes

Reaction equation

HRID 2216731 reaction equation
[CH3:1][CH:2]1[CH2:21][C:5]2[S:6][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:4]=2[C:3]1=[O:22].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC>[CH3:1][CH:2]1[CH2:21][C:5]2[S:6][C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:4]=2[CH:3]1[OH:22]

Participants

5

Reactant 3

HCID 962Water2×HCID 21226445Aluminium lithium hydrideHCID 21943908HCID 21943908, compound

Product 1

HCID 67174670HCID 67174670, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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).

Workup

  1. extractionwas extracted with ether (3×50 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated off to dryness

Sources & evidence

ORD record
ord-b7df18dab4874e4e82cd34c4bfe27e29
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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