3-Benzoyloxy-5-t-butyldimethylsiloxycyclopent-1-ene → 2-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 2163165Notes

Reaction equation

HRID 2163165 reaction equation
C([O:9][CH:10]1[CH2:14][CH:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[CH:11]1)(=O)C1C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[O:15]([CH:13]1[CH2:14][CH:10]([OH:9])[CH:11]=[CH:12]1)[Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 146847773-Benzoyloxy-5-t-butyldimethylsiloxycyclopent-1-eneHCID 21226445Aluminium lithium hydride

Product 1

HCID 127633552-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-Yield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

By operating as in Example 25, 140 milligrams (0.44 mmol) of 3-benzoyloxy-5-t-butyldimethylsiloxycyclopent-1-ene was held in anhydrous ether with 30 milligrams (0.79 mmol) of lithium aluminum hydride for one hour at room temperature under a nitrogen atmosphere, following which the mixture was heated under reflux for 30 minutes. Thereafter the aftertreatment was carried out as in Example 25, and the resulting crude product was separated by preparative thin-layer chromatograph (silica gel 2mm, hexane:ethyl acetate = 4:1) to obtain 85 milligrams (0.04 mmol, 91%) of 3-t-butyldimethylsiloxy-5-hydroxycyclopent-1-ene.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customthe resulting crude product was separated by preparative thin-layer chromatograph (silica gel 2mm, hexane:ethyl acetate = 4:1)

Sources & evidence

ORD record
ord-dbc1ec10135144c19b14fd296d2d4dc2
Source dataset
uspto-grants-1979_01
Patent number
US04132726

Reaction notes

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