2-(1-methylindol-2-yl)propan-2-ol → HCID 10464759, compound

HRID 373996Notes

Reaction equation

HRID 373996 reaction equation
O[C:2]([C:5]1[N:6]([CH3:14])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([CH3:4])[CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:2]([C:5]1[N:6]([CH3:14])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 2956452-(1-methylindol-2-yl)propan-2-olHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 10464759HCID 10464759, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.0 g of 2-(1-hydroxy-1-methylethyl)-1-methylindole was dissolved in 80 ml of toluene. Thereto was added 200 mg of p-toluenesulfonic acid monohydrate. The mixture was azeotropically refluxed for 2 hours. The reaction mixture was cooled to room temperature, washed with an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: n-hexane/toluene=1/0 to 20/1) to obtain 850 mg (yield: 24%) of 2-isopropenyl-1-methylindole as a light yellow oily material.

Workup

  1. temperatureThe mixture was azeotropically refluxed for 2 hours
  2. washwashed with an aqueous saturated sodium hydrogencarbonate solution
  3. dry with materialan aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluant: n-hexane/toluene=1/0 to 20/1)

Sources & evidence

ORD record
ord-5a48357e72464a30a0a416744e65ab50
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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