Methyl iodide → HCID 10192771, compound

HRID 495114Notes

Reaction equation

HRID 495114 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[CH3:11][C:12]1([CH3:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[CH2:13]1.[CH3:23]I>C1COCC1.O.CCO>[CH2:8]([O:7][C:3]([C:13]1([CH3:23])[C:14](=[O:21])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]1([CH3:22])[CH3:11])=[O:10])[CH3:9]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 3046283,3-Dimethyl-1-indanone

Product 1

HCID 10192771HCID 10192771, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To the suspension of NaH (3.05 g at 55% in mineral oil, 70 mmol, 1.4 equiv.) in THF (25 ml) was added neat diethyl carbonate (23.6 g, 200 mmol, 4 equiv.) followed by a solution of 3,3-dimethyl-1-indanone (8.0 g, 50 mmol, 1 equiv.) in THF (25 ml). The mixture was heated to 80° C. for 16 h, then cooled to 50° C. and treated with methyl iodide (21.3 g, 150 mmol, 3 equiv.). After 4.5 h further stirring at 50° C. the mixture was cooled to 5° C. and EtOH (20 ml) followed by H2O (20 ml) was introduced. After dilution with MTBE the phases were separated and the organic layer washed twice with brine, then dried over MgSO4. The residue obtained after concentration in a rotary evaporator was subjected to a short path distillation at 0.05 mbar and 90-115° C., followed by a fine distillation at 0.05 mbar, 112-116° C. to yield the product as a colourless oil (6.5 g, 53%).

Workup

  1. temperaturecooled to 50° C.
  2. temperaturewas cooled to 5° C.
  3. additionwas introduced
  4. customAfter dilution with MTBE the phases were separated
  5. washthe organic layer washed twice with brine
  6. dry with materialdried over MgSO4
  7. customThe residue obtained
  8. concentrationafter concentration
  9. customin a rotary evaporator
  10. distillationwas subjected to a short path distillation at 0.05 mbar and 90-115° C.
  11. distillationfollowed by a fine distillation at 0.05 mbar, 112-116° C.

Sources & evidence

ORD record
ord-679a306a9d884ab9b3f1d2580745654c
Source dataset
uspto-grants-2009_05
Patent number
US07538243B2

Reaction notes

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