Water → HCID 68999415, compound

HRID 1784332Notes

Reaction equation

HRID 1784332 reaction equation
[CH3:1][CH:2]1[CH2:20][C:5]2[C:6]3[C:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:12][CH:11]=[CH:10][C:7]=3[S:8](=O)[C:4]=2[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.C(OCC)C.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH2:20][C:5]2[C:6]3[C:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:12][CH:11]=[CH:10][C:7]=3[S:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 21226445Aluminium lithium hydrideHCID 69003499HCID 69003499, compound

Product 1

HCID 68999415HCID 68999415, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 81.4 g of 2-methyl-8-phenyl-1,2-dihydrobenzo[b]cyclopenta[d]thiophenone (0.29 mol) (1a) in 800 ml of THF was admixed at 0° C. with 225 ml of a 1.0 molar solution of lithium aluminum hydride (0.23 mol) in diethyl ether. The mixture was stirred at room temperature for another 4 hours. 25 ml of water were then carefully added and the resulting suspension was filtered through a layer of Celite and dried over magnesium sulfate. After filtration, the solvent was removed and a brown vitreous solid was obtained. The solid was dissolved in 400 ml of toluene and, after addition of 2.0 g of p-toluenesulfonic acid, stirred at 70° C. for 2 hours. The cooled reaction mixture was washed with a saturated solution of sodium hydrogencarbonate and with water and dried over magnesium sulfate. After the desiccant had been separated off, the solvent was removed and the residue was chromatographed on silica gel (5% methylene chloride in hexane as eluant). This gave 39 g (52%) of (1b) as a light-yellow oil.

Workup

  1. filtrationthe resulting suspension was filtered through a layer of Celite
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was removed
  5. customa brown vitreous solid was obtained
  6. stirringstirred at 70° C. for 2 hours
  7. customThe cooled reaction mixture
  8. washwas washed with a saturated solution of sodium hydrogencarbonate and with water
  9. dry with materialdried over magnesium sulfate
  10. customAfter the desiccant had been separated off
  11. customthe solvent was removed
  12. customthe residue was chromatographed on silica gel (5% methylene chloride in hexane as eluant)

Sources & evidence

ORD record
ord-ddbb201535134dad8e2a408140bc94af
Source dataset
uspto-grants-2009_03
Patent number
US07504354B2

Reaction notes

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