Water → 5,5-Diphenyl-2-cyclopenten-1-ol

HRID 1657262Notes

Reaction equation

HRID 1657262 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11](=[O:12])[CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Ce+3].[BH4-].[Na+].O>CO.C(Cl)Cl.C(O)C>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]([OH:12])[CH:10]=[CH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24636Cerium(III) chloride2×HCID 4311764Sodium borohydride2×HCID 104665565,5-Diphenyl-2-cyclopenten-1-one

Product 1

HCID 100371165,5-Diphenyl-2-cyclopenten-1-olYield 82.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5,5-diphenyl-2-cyclopenten-1-one (1.0 g) and cerium trichloride 7 hydrate (1.59 g) in methanol (10 ml) and methylene chloride (4 ml) was added dropwise a solution of sodium borohydride (0.16 g) in ethanol (6 ml) at 0° C. to 3° C. To the reaction mixture, cerium trichloride 7 hydrate (0.80 g) and sodium borohydride (0.08 g) were added 4 times an hour. After the reaction finished, cold water (30 ml) was added, and the mixture was extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with methylene chloride as an eluent to give 5,5-diphenyl-2-cyclopenten-1-ol 0.83 g).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with methylene chloride as an eluent

Sources & evidence

ORD record
ord-25c1f7bdbaf04d8e8422fcea38e1e35f
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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