Methyl iodide → HCID 59199412, compound

HRID 2089547Notes

Reaction equation

HRID 2089547 reaction equation
[F-].[K+].[Cl:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:14])C[C:8]2=[O:13].I[CH3:16].[C:17](#N)[CH3:18]>>[Cl:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:14])[C:17]([CH3:18])([CH3:16])[C:8]2=[O:13]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 522689Potassium FluorideHCID 123842804-Chloro-1H-indene-1,3(2H)-dione

Product 1

HCID 59199412HCID 59199412, compound

Procedure

Potassium fluoride on Celite® [loading wt: 50% purchased from Sigma-Aldrich Co.] (17.4 g, ˜150 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 4-chloro-indan-1,3-dione (CAS#20926-88-9, 5.6 g, 31.0 mmol), which can be prepared as described by Smith, H.; et al. Journal of Medicinal Chemistry, 1973, 16, 1334-1339, in acetonitrile (45 mL) is added. Iodomethane (5.4 mL, 90 mmol) is then added to the mixture. 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 reaction mixture is cooled to room temperature and filtered through a pad of Celite®. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9) to furnish 4-chloro-2,2-dimethyl-indan-1,3-dione; 1H NMR (400 MHz, CDCl3) δ ppm 1.32 (s, 6 H), 7.74-7.82 (m, 2 H), 7.91 (dd, J=7.1, 1.5 Hz, 1 H).

Workup

  1. customcan be prepared
  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. temperaturethe reaction mixture is cooled to room temperature
  7. filtrationfiltered through a pad of Celite®
  8. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9)

Sources & evidence

ORD record
ord-0fae7b0032774894862c9e3e7ab97d9c
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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