Methyl iodide → 2,2-Dimethyl-4-methoxyindanone

HRID 1253152Notes

Reaction equation

HRID 1253152 reaction equation
OC1[CH:10]=[CH:9][CH:8]=[C:7]2C=1[CH2:4][CH2:5][C:6]2=[O:11].[H-].[Na+].[CH3:14]I.[CH2:16]1[CH2:20][O:19][CH2:18][CH2:17]1>>[CH3:14][C:5]1([CH3:4])[CH2:17][C:16]2[C:7](=[CH:8][CH:9]=[CH:10][C:20]=2[O:19][CH3:18])[C:6]1=[O:11]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 136929432,2-Dimethyl-4-methoxyindanone

Procedure

4-Hydroxy-indanone (25 g) is added portionwise to a stirred suspension of sodium hydride (40.1 g, 60% in mineral oil) and methyl iodide (62.4 g) in anhydrous THF (990 ml) under nitrogen and the mixture is stirred at RT overnight. The reaction mixture is quenched with H2O, washed with diethyl ether and the etheral layer is washed with 10% aq. NaHSO3 and H2O, dried, filtered, and evaporated. The residue is chromatographed (silica gel; eluent=hexane/EtOAC) affording the desired product as a solid.

Workup

  1. customThe reaction mixture is quenched with H2O
  2. washwashed with diethyl ether
  3. washthe etheral layer is washed with 10% aq. NaHSO3 and H2O
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed (silica gel; eluent=hexane/EtOAC)

Sources & evidence

ORD record
ord-250131df0d94464e8b40fdef2c6643e9
Source dataset
uspto-grants-1988_05
Patent number
US04748164

Reaction notes

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