Water → HCID 10423493, compound

HRID 1455699Notes

Reaction equation

HRID 1455699 reaction equation
[CH2:1]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[C:12](=O)[CH2:11][CH2:10]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[CH3:21]I.O.CN(C)[CH:26]=[O:27]>>[CH2:1]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[C:26](=[O:27])[C:11]([CH3:12])([CH3:21])[CH2:10]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 12144845HCID 12144845, compound

Product 1

HCID 10423493HCID 10423493, compound

Conditions

Temperature
25 °C

Procedure

5 g (0.02 mol) of 5-hexyl-6-methoxyindan-1-one dissolved in 20 ml of dimethylformamide are added dropwise to a suspension of 1.8 g (0.04 mol) of sodium hydride in 20 ml of dimethylformamide at 25° C. The mixture is stirred for 15 minutes at this temperature, and 11.4 g (0.1 mol) of methyl iodide are then added, while maintaining the temperature below 30° C. The reaction medium is stirred for 16 hours at 25° C. A further 0.9 g (0.0375 mol) of sodium hydride is added, and 15 minutes later 11.4 g (0.1 mol) of methyl iodide are added and the mixture is stirred for 2 hours at 25° C. The mixture is then heated for 1 hour at 50° C. It is poured into water and extracted with ether. The organic phase is dried (Na2SO4) and then evaporated under reduced pressure. The orange oil obtained is purified by flash chromatography (dichloromethane, 3.54 g; 65%).

Workup

  1. additionare then added
  2. temperaturewhile maintaining the temperature below 30° C
  3. stirringthe mixture is stirred for 2 hours at 25° C
  4. temperatureThe mixture is then heated for 1 hour at 50° C
  5. extractionextracted with ether
  6. dry with materialThe organic phase is dried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customThe orange oil obtained
  9. customis purified by flash chromatography (dichloromethane, 3.54 g; 65%)

Sources & evidence

ORD record
ord-0d2e5751e1c8415a978356668551c876
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

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