Methanol → 6-Methyl-4,8-diphenyl-1,2,3,5-tetrahydro-s-indacene

HRID 271800Notes

Reaction equation

HRID 271800 reaction equation
[CH3:1][CH:2]1[CH2:13][C:12]2[C:4](=[C:5]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[C:11]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]1=O.[BH4-].[Na+].CO>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH2:13][C:12]2[C:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:10]3[C:6](=[C:5]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:4]=2[CH:3]=1)[CH2:7][CH2:8][CH2:9]3

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 687444242-methyl-4,8-diphenyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

Product 1

HCID 860577626-Methyl-4,8-diphenyl-1,2,3,5-tetrahydro-s-indacene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

17.4 g (51 mmol) of 2-methyl-4,8-diphenyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one (4b) and 3.8 g (100 mmol) of sodium borohydride in 100 ml of toluene were placed in a reaction vessel. The solution was heated to 50° C. and 22 ml of methanol was slowly added and the reaction mixture was stirred at 50° C. for 3 hours and then at room temperature overnight. During stirring solids were precipitated. 12 ml of water and 80 ml of 1 N sulfuric acid were added and the mixture was stirred at 35° C. for 30 minutes. 200 ml of methylene chloride was added and organic phase was separated and evaporated and the residue (18.0 g) was taken up in 200 ml of toluene and mixed with 100 mg of p-toluenesulfonic acid. Water was distilled off from this reaction mixture by refluxing for 1 hour on a water separator until reaction was complete. The reaction mixture was washed once with 100 ml of saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. After removal of the solvent, the residue was dried in an oil pump vacuum. This gave 18 g of pale brawn solid. The crude product was purified by column chromatography.

Workup

  1. customat room temperature
  2. customovernight
  3. stirringDuring stirring solids
  4. customwere precipitated
  5. addition12 ml of water and 80 ml of 1 N sulfuric acid were added
  6. stirringthe mixture was stirred at 35° C. for 30 minutes
  7. addition200 ml of methylene chloride was added
  8. customorganic phase was separated
  9. customevaporated
  10. additionmixed with 100 mg of p-toluenesulfonic acid
  11. distillationWater was distilled off from this reaction mixture
  12. temperatureby refluxing for 1 hour on a water separator until reaction
  13. washThe reaction mixture was washed once with 100 ml of saturated sodium hydrogen carbonate solution
  14. dry with materialdried over magnesium sulfate
  15. customAfter removal of the solvent
  16. customthe residue was dried in an oil pump vacuum
  17. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-557af66649c840dd9dc876145834322c
Source dataset
uspto-grants-2008_11
Patent number
US07452949B2

Reaction notes

Loading…