Chloride → HCID 54308991, compound

HRID 2051421Notes

Reaction equation

HRID 2051421 reaction equation
[Cl-].CC([O-])(C)C.[K+].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:24])=[C:14]2[C:22]=1[C:21](=O)[CH:20]1[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]1.O.[O:26]1[CH2:31]COC[CH2:27]1>>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:24])=[C:21]2[C:22]=1[C:14](=[CH:27][O:26][CH3:31])[CH:15]1[CH:20]2[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 5

HCID 312ChlorideHCID 962WaterHCID 312751,4-DioxaneHCID 15157182HCID 15157182, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54308991HCID 54308991, compound

Procedure

50.00 Grams of methoxymethyltriphenylphosphnium chloride was suspended in 400 ml of dioxane and 16.37 g of t-BuOK was added thereto under ice-cooling and nitrogen atmosphere, followed by stirring at room temperature for 2 hours. To this dark red solution was added 6.72 g of 8-methoxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone, followed by further stirring at room temperature for 2 hours. Then, the reaction mixture was refluxed for 3 hours and left to stand for cooling. Thereafter, 400 ml of water was added and extraction was effected with diethyl ether. The organic layer was dried with magnesium sulfate, filtered and concentrated. The residue was purified by a silica gel column chromatography (eluent:n-hexane) to obtain 4.54 g of 8-methoxy-9-methoxymethylene-5-methyl-1,2,3,4,4a,9a-hexahydrofluorene which was a yellow oily substance.

Workup

  1. temperatureunder ice-cooling
  2. stirringby further stirring at room temperature for 2 hours
  3. temperatureThen, the reaction mixture was refluxed for 3 hours
  4. waitleft
  5. temperaturefor cooling
  6. extractionextraction
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by a silica gel column chromatography (eluent:n-hexane)

Sources & evidence

ORD record
ord-30b8008527134e9787fd38f35ad06927
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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