Hydrochloric Acid → 4,4-Diphenyl-2-cyclopenten-1-ol

HRID 1657275Notes

Reaction equation

HRID 1657275 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][C:10](=[O:12])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=O)C.Cl>C1(C)C=CC=CC=1.CCCCCC>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH:10]([OH:12])[CH:9]=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 108898542-Cyclopenten-1-one, 4,4-diphenyl-HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 108237324,4-Diphenyl-2-cyclopenten-1-olYield 95.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4,4-diphenyl-2-cyclopenten-1-one (0.30 g) in toluene (3 ml) was added a 1M solution of diisobutylaluminum hydride in n-hexane (2.0 ml) at -5° C. to 4° C. After being stirred for 20 minutes, ethyl acetate (3 ml) and 10% hydrochloric acid (2 ml) was added to the solution successively, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with methylene chloride as an eluent to give 4,4-diphenyl-2-cyclopenten-1-ol (0.29 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over sodium 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-5757759cdda3493f844dfc193f802b64
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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