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

HRID 1905751Notes

Reaction equation

HRID 1905751 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-42fd7a4ba83a48048ce973215e0783fc
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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