Methanol → HCID 57723635, compound

HRID 1919791Notes

Reaction equation

HRID 1919791 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[C:6]2=O.[BH4-].[Na+].CO.OS(O)(=O)=O>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:13])[CH2:6]2

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 22173403HCID 22173403, compound

Product 1

HCID 57723635HCID 57723635, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a 250 ml round bottom flask 19.2 g (63 mmol) 4,7-Dibromo-2-methyl-indan-1-one were dissolved in 70 ml of toluene at 50° C. Then 2.63 g (1.1 eq.) sodium borohydride were added. At 50° C. 11 ml (4.3 eq.) methanol were added dropwise over a period of 30 min. Stirring was continued at 50° C. for 3 h (complete conversion) and then 50 ml water and 50 ml of 2M H2SO4 were added. The aqueous phase was extracted 2 times with 100 ml toluene. The combined organic layers were washed with 50 ml 2M H2SO4 and 50 ml of a sodium chloride solution, dried over magnesium sulfate and the solvent was removed in vacuo. 200 ml toluene and 200 mg p-toluene sulfonic acid were added and the solution was heated on a Dean-Stark-trap for 90 min. 50 ml of a saturated sodium bicarbonate solution were added. The aqueous layer was extracted 2 times with 50 ml toluene each. The combined organic layers were washed with 50 ml of a saturated sodium bicarbonate solution and 50 ml of a sodium chloride solution, dried over magnesium sulfate and the solvent was removed in vacuo to yield 17.8 g (62 mmol, 98%) of the desired indene as a slightly brown oil. 1H-NMR (500 MHz, CDCl3): δ=7.48, 7.35 (2×d, 2H, aromatic), 6.49 (s, 1H, indenyl-C═CH), 3.32 (s, 2H, benzylic), 2.12 (2, 3H, CH3) ppm.

Workup

  1. customAt 50° C
  2. extractionThe aqueous phase was extracted 2 times with 100 ml toluene
  3. washThe combined organic layers were washed with 50 ml 2M H2SO4 and 50 ml of a sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. addition200 ml toluene and 200 mg p-toluene sulfonic acid were added
  7. temperaturethe solution was heated on a Dean-Stark-trap for 90 min
  8. addition50 ml of a saturated sodium bicarbonate solution were added
  9. extractionThe aqueous layer was extracted 2 times with 50 ml toluene each
  10. washThe combined organic layers were washed with 50 ml of a saturated sodium bicarbonate solution and 50 ml of a sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cb2f314b4b0a457b87beaf3b1dd22214
Source dataset
uspto-grants-2012_05
Patent number
US08168556B2

Reaction notes

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