Methyl iodide → 2,2-Dimethyl-1H-indene-1,3(2H)-dione

HRID 2089501Notes

Reaction equation

HRID 2089501 reaction equation
[F-].[K+].[C:3]1(=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])C1.I[CH3:15].[C:16](#N)[CH3:17]>>[CH3:15][C:16]1([CH3:17])[C:3](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:12]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 118151,3-IndandioneHCID 522689Potassium Fluoride

Product 1

HCID 5999832,2-Dimethyl-1H-indene-1,3(2H)-dione

Procedure

Potassium fluoride on Celite® [loading wt: 50% purchased from Sigma-Aldrich Co.] (5.8 g, ˜50 mmol) is heated at 135° C. for 2 hours under vacuum (<20 torr). The solid is then permitted to cool to room temperature and placed under a nitrogen atmosphere at which time a solution of indan-1,3-dione (CAS#606-23-5, 1.46 g, 10.0 mmol) in acetonitrile (15 mL) is added followed by iodomethane (1.8 mL, 30 mmol). The reaction is heated in a sealed vessel at 70° C. overnight. The reaction mixture is cooled to room temperature and filtered through a pad of Celite®. The eluent is concentrated and the resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9) to furnish 2,2-dimethyl-indan-1,3-dione 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (s, 6 H), 7.84-7.89 (m, 2 H), 7.96-8.02 (m, 2 H).

Workup

  1. additionis added
  2. temperatureThe reaction is heated in a sealed vessel at 70° C. overnight
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered through a pad of Celite®
  5. concentrationThe eluent is concentrated
  6. customthe resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9)

Sources & evidence

ORD record
ord-5d4b25ff3ceb459e882a481fcb8e2be5
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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