Diethyl Ether → Octahydro-2H-inden-2-one

HRID 2107798Notes

Reaction equation

HRID 2107798 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]1[CH:20]2[CH:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:14][CH:13]1[OH:21].CCOCC>ClCCl>[CH2:12]1[CH:20]2[CH:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:14][C:13]1=[O:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12537367Octahydro-1H-inden-2-olHCID 178418287HCID 178418287, compound

Product 1

HCID 138565Octahydro-2H-inden-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To 33.6 g (155 mmol) of finely ground pyridinium chlorochromate, stirred in 300 mL of dry dichloromethane, was added 7.0 g (50 mmol) of (2 alpha and 2 beta)-octahydro-1H-inden-2-ol in 30 mL of dichloromethane. After stirring for 2 h at 20° C., 300 mL of ether was added, the organic solution decanted from the gummy precipitate and the latter extracted with 5×100 mL of ether. The combined organic solutions were filtered through 450 g of silica gel and the latter washed with ether. Concentration of the filtrates and distillation gave 5.5 g (80%) of (3a alpha, 7a alpha)octahydro-2H-inden-2-one bp 110°-112° C. (18 mm); TLC Rf of 0.29 (SiO2, dichloromethane, molybdophosphoric acid-colorless on blue-green).

Workup

  1. customthe organic solution decanted from the gummy precipitate
  2. extractionthe latter extracted with 5×100 mL of ether
  3. filtrationThe combined organic solutions were filtered through 450 g of silica gel
  4. washthe latter washed with ether
  5. distillationConcentration of the filtrates and distillation

Sources & evidence

ORD record
ord-e5cd38013b7248e8ba8b81f25dc216e6
Source dataset
uspto-grants-1990_06
Patent number
US04935509

Reaction notes

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