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

HRID 271795Notes

Reaction equation

HRID 271795 reaction equation
[C:1]1([C:7]2[C:18]3[CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=[C:12]3[C:8]=2[CH2:9][CH:10]([CH3:20])[C:11]3=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].CO.S(=O)(=O)(O)O>C1(C)C=CC=CC=1.O>[C:1]1([C:7]2[C:8]3[CH2:9][C:10]([CH3:20])=[CH:11][C:12]=3[CH:13]=[C:14]3[C:18]=2[CH2:17][CH2:16][CH2:15]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 235470482-methyl-4-phenyl-2,3,6,7-tetrahydro-s-indacen-1(5H)-one

Product 1

HCID 534453466-Methyl-4-phenyl-1,2,3,5-tetrahydro-s-indacene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

9.6 g (24.4 mmol) of 4-phenyl-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one (2a) and 2.10 g (55 mmol) of sodium borohydride in 40 ml of toluene were placed in a reaction vessel. The solution was heated to 50° C. and 7 ml of methanol was added slowly and the reaction mixture was stirred at 50° C. for 3 hours. After cooling to room temperature 12 ml of water and 40 ml of 1 N sulfuric acid were added and the mixture was stirred for 30 minutes. After phase separation the water phase was extracted with toluene. Organic phase was evaporated and the residue was taken up in 100 ml of toluene and mixed with 100 mg of p-toluenesulfonic acid. Water was distilled off from this reaction mixture by refluxing for 2 hours 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 11.5 g of brawn oil. The crude product was purified by column chromatography (200 g of silica gel, 1 l of heptane: diethylether=9:1).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 30 minutes
  3. customAfter phase separation the water phase
  4. extractionwas extracted with toluene
  5. customOrganic phase was evaporated
  6. additionmixed with 100 mg of p-toluenesulfonic acid
  7. distillationWater was distilled off from this reaction mixture
  8. temperatureby refluxing for 2 hours on a water separator until reaction
  9. washThe reaction mixture was washed once with 100 ml of saturated sodium hydrogen carbonate solution
  10. dry with materialdried over magnesium sulfate
  11. customAfter removal of the solvent
  12. customthe residue was dried in an oil pump vacuum
  13. customThe crude product was purified by column chromatography (200 g of silica gel, 1 l of heptane: diethylether=9:1)

Sources & evidence

ORD record
ord-ef0e3911ddbb4f328dbfcce54d23e17c
Source dataset
uspto-grants-2008_11
Patent number
US07452949B2

Reaction notes

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