Cyclohexene → HCID 23579094, compound

HRID 1827305Notes

Reaction equation

HRID 1827305 reaction equation
C1CCCCC=1.[C:7]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C@@H:22]1[O:36][C@:26]2([CH2:37][O:38]CC3C=CC=CC=3)[C@@:27](CC3C=CC=CC=3)([OH:28])[C@H:23]1[O:24][CH2:25]2)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[OH-].[Pd+2].[OH-].[C].C(O)C>[C:7]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C@@H:22]1[O:36][C@:26]2([CH2:37][OH:38])[C@@H:27]([OH:28])[C@H:23]1[O:24][CH2:25]2)(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 131725776HCID 131725776, compound

Product 1

HCID 23579094HCID 23579094, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 702EthanolSolvent

Procedure

In a stream of nitrogen, 20% palladium hydroxide-carbon (53 mg) and cyclohexene (0.52 ml, 5.1 mmols) were added to an anhydrous ethanol (2 ml) solution of the compound (25) (54 mg, 0.10 mmol), and the mixture was heated under reflux for 2 hours. After filtration, the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform:methanol=80:3) to obtain a white powder (26) (30 mg, 85%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationAfter filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (chloroform:methanol=80:3)

Sources & evidence

ORD record
ord-8cdfa484669a4173a9374bd739e1b02e
Source dataset
uspto-grants-2006_05
Patent number
US07053199B2

Reaction notes

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