z1-Indanone, 5,6-dimethoxy-3,3-dimethyl- → 5,6-Dimethoxy-1,1-dimethylindene

HRID 2306790Notes

Reaction equation

HRID 2306790 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:10](=O)[CH2:9][C:8]2([CH3:18])[CH3:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:15][O:14][C:13]1[CH:12]=[C:11]2[C:7](=[CH:6][C:5]=1[O:4][CH3:3])[C:8]([CH3:18])([CH3:17])[CH:9]=[CH:10]2

Participants

5

Reactant 3

HCID 138129z1-Indanone, 5,6-dimethoxy-3,3-dimethyl-HCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydride

Product 1

HCID 226095985,6-Dimethoxy-1,1-dimethylindeneYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 1.1 g (28 mmol) of sodium borohydride were added to a solution of 1.9 g (9.2 mmol) of 5,6-dimethoxy-3,3-dimethylindan-1-one in methanol (30 ml), and the mixture was stirred for 5 minutes at room temperature. After methanol was removed from the reaction mixture by concentration under reduced pressure, water was added to the residue, and the mixture was extracted with diethyl ether. An organic layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. Added to a solution of the resultant residue in toluene (50 ml) was 90 mg (0.47 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was stirred for 20 minutes at 120° C. The reaction mixture was concentrated under reduced pressure, and the resultant crude oil was purified by column chromatography on silica gel to obtain 264 mg (yield: 15%) of 5,6-dimethoxy-1,1-dimethylindene as a colorless oil.

Workup

  1. customAfter methanol was removed from the reaction mixture by concentration under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with diethyl ether
  4. washAn organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionAdded to a solution of the resultant residue in toluene (50 ml)
  8. stirringthe mixture was stirred for 20 minutes at 120° C
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-36284111a97148b29e5ca0e483b06876
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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