HCID 178477217, compound → HCID 178477216, compound

HRID 1456350Notes

Reaction equation

HRID 1456350 reaction equation
C([O:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[CH2:12][CH2:11]1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([CH:16]([O:18][Si:19]([C:22]([CH3:23])([CH3:25])[CH3:24])([CH3:21])[CH3:20])[CH3:17])[CH2:14][CH2:15]1

Participants

4

Reactant 1

HCID 178477217HCID 178477217, compound

Product 1

HCID 178477216HCID 178477216, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst3×HCID 702EthanolSolvent

Procedure

In 50 ml of dry ethanol was dissolved 2.7 g of trans-4-benzyloxymethyl-1-(1-t-butyldimethylsilyloxyethyl)cyclohexane, and 2.0 g of 10% palladium-carbon was added thereto, and the resulting mixture was heated under reflux for 9 hours and 50 minutes while stirring under a hydrogen stream. Further, 2.0 g of 10% palladium-carbon was added to the reaction mixture and the resulting mixture was heated under reflux for 4 hours and 15 minutes while stirring under a hydrogen stream. After completion of the reaction, palladium-carbon was separated by filtration and the solvent was distilled off under reduced pressure to obtain 1.85 g of the desired compound as a colorless oil.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 9 hours and 50 minutes
  4. temperaturethe resulting mixture was heated
  5. temperatureunder reflux for 4 hours and 15 minutes
  6. stirringwhile stirring under a hydrogen stream
  7. customwas separated by filtration
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a244cd20772f442f8560e821dd41a92f
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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