Methyl iodide → HCID 11535657, compound

HRID 2242542Notes

Reaction equation

HRID 2242542 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6]C=CC=2)[C:4](=O)CC1.I[CH3:13].C[C:15]([CH3:18])([O-:17])[CH3:16].[K+].O1C[CH2:23][CH2:22][CH2:21]1>>[CH3:13][C:5]1([CH3:4])[C:10](=[O:1])[C:18]2[C:15](=[CH:16][CH:21]=[CH:22][CH:23]=2)[O:17][CH2:6]1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 68110ChromanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 11535657HCID 11535657, compoundYield 100%

Procedure

To a cooled (−78° C. bath temperature) solution of 2,3-dihydro-4H-chromen-4-one (25 grams, 0.169 mole) and iodomethane (120 grams, 53 ml, 0.945 mole) in anhydrous tetrahydrofuran (1000 ml) was added portion-wise potassium tertiary butoxide (94.5 grams, 0.945 mole) over a period of 1 hour under an argon atmosphere. During this process, the reaction temperature was kept at −78° C. to avoid exothermic reaction. The cooling bath was removed, and the resulting mixture was warmed to room temperature over a period of 4 hours. The white viscous mixture was heated at 60° C. (bath temperature) for 4 hours, cooled to room temperature, and stirred at room temperature for 15 hours. The resulting mixture was poured into a mixture of diethyl ether and water. The organic layer was separated, and the aqueous layer was extracted with diethyl ether. The combined extracts were washed with saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The residue was chromatographed (silica gel, elution by methylene chloride) to give 30 grams (100%) of 3,3-dimethyl-2,3-dihydro-4H-chromen-4-one as a clear pale yellow oil. Physical properties of the product were the same as those described in Example 3.

Workup

  1. customwas kept at −78° C.
  2. customreaction
  3. customThe cooling bath was removed
  4. temperatureThe white viscous mixture was heated at 60° C. (bath temperature) for 4 hours
  5. temperaturecooled to room temperature
  6. additionThe resulting mixture was poured into a mixture of diethyl ether and water
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with diethyl ether
  9. washThe combined extracts were washed with saturated sodium chloride aqueous solution
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was chromatographed
  13. wash(silica gel, elution by methylene chloride)

Sources & evidence

ORD record
ord-4d18506015d84d619c76f43b7fd6b848
Source dataset
uspto-grants-2010_03
Patent number
US07671220B2

Reaction notes

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