3-(4-tert-Butylphenyl)-2-methylcyclopent-2-en-1-one → HCID 19889538, compound

HRID 653686Notes

Reaction equation

HRID 653686 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:15][CH2:14][C:13](=[O:16])[C:12]=2[CH3:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC.C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH2:15][CH2:14][CH:13]([OH:16])[C:12]=2[CH3:17])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 198895313-(4-tert-Butylphenyl)-2-methylcyclopent-2-en-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 19889538HCID 19889538, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 25.7 g (0.12 mol) of 3-(4-t-butylphenyl)-2-methyl-2-cyclopenten-1-one (EP 0259977) dissolved in 40 mL of ether was cooled to 0° C. Added dropwise was 43.7 mL (43.7 mmol) of a solution of 1M lithium aluminum hydride in THF. After stirring 20 min, the mixture was quenched by dropwise addition of saturated aqueous NaHSO3. The mixture was dried (MgSO4), solids were filtered and the filtrate was stripped to afford 26.8 g of 1-(4-t-butylphenyl)-2-methyl-cyclopenten-3-ol as an oil which slowly solidified.

Workup

  1. customthe mixture was quenched by dropwise addition of saturated aqueous NaHSO3
  2. dry with materialThe mixture was dried (MgSO4), solids
  3. filtrationwere filtered

Sources & evidence

ORD record
ord-3e1013c60f214365a267286b5c195ec4
Source dataset
uspto-grants-1992_07
Patent number
US05128348

Reaction notes

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