Water → HCID 21943888, compound

HRID 2216723Notes

Reaction equation

HRID 2216723 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[CH3:12].[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[CH3:12]

Participants

5

Reactant 3

HCID 962Water2×HCID 21226445Aluminium lithium hydrideHCID 21943916HCID 21943916, compound

Product 1

HCID 21943888HCID 21943888, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,3,5-trimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-4-one (11 g, 61 mmol) in 100 mL of ether was slowly added to a solution of LiAlH4 (1.16 g, 30 mmol) in 100 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 2,3,5-trimethyl-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. Yield 8 g (80% based on 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-1b6cb8b6d265429aa2b22798a8eb4a14
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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