Diethyl Ether → HCID 11535657, compound

HRID 2242541Notes

Reaction equation

HRID 2242541 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6]C=CC=2)[C:4](=O)CC1.IC.C[C:15]([CH3:18])([O-:17])[CH3:16].[K+].[CH2:20](OCC)C.O1C[CH2:28][CH2:27][CH2:26]1>O>[CH3:20][C:5]1([CH3:4])[C:10](=[O:1])[C:18]2[C:15](=[CH:16][CH:26]=[CH:27][CH:28]=2)[O:17][CH2:6]1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6328Methyl iodide2×HCID 8028TetrahydrofuranHCID 68110ChromanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 11535657HCID 11535657, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (−10 to 0° C. bath temperature) solution of 2,3-dihydro-4H-chromen-4-one (8.0 grams, 0.054 mole) and iodomethane (22.8 grams, 10 ml, 0.16 mole) in anhydrous tetrahydrofuran (150 ml) was added portion-wise potassium tertiary butoxide (30 grams, 0.27 mole) under an argon atmosphere. During this process, the temperature was kept between −10 to 0° C. to avoid exothermic reaction. The cooling bath was removed, and the resulting mixture was warmed to room temperature. The mixture was heated at 60° C. for 4 hours, heated at reflux for 1 hour, and cooled to room temperature. Additional iodomethane (16 grams, 7 ml, 0.11 mole) was added, and heating was repeated at 60° C. for 4 hours and at reflux for 1 hour. The cooled solution 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 5.62 grams (59.1%) of 3,3-dimethyl-2,3-dihydro-4H-chromen-4-one as a clear pale yellow oil.

Workup

  1. customwas kept between −10 to 0° C.
  2. customreaction
  3. customThe cooling bath was removed
  4. temperatureThe mixture was heated at 60° C. for 4 hours
  5. temperatureheated
  6. temperatureat reflux for 1 hour
  7. temperaturecooled to room temperature
  8. temperatureheating
  9. temperatureat reflux for 1 hour
  10. customThe organic layer was separated
  11. extractionthe aqueous layer was extracted with diethyl ether
  12. washThe combined extracts were washed with saturated sodium chloride aqueous solution
  13. dry with materialdried over sodium sulfate
  14. concentrationconcentrated
  15. customThe residue was chromatographed
  16. wash(silica gel, elution by methylene chloride)

Sources & evidence

ORD record
ord-bbceb0a8068a48dd9ebb81e1da26b7a1
Source dataset
uspto-grants-2010_03
Patent number
US07671220B2

Reaction notes

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