Dimethyl Carbonate → HCID 59835936, compound

HRID 271546Notes

Reaction equation

HRID 271546 reaction equation
[S:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[S:4][CH2:3][CH2:2]1.[H-].[Na+].[C:14](=O)([O:17]C)[O:15][CH3:16]>C1COCC1>[CH3:16][O:15][C:14]([C:9]1[CH2:10][C:5]2([CH2:6][CH2:7][C:8]=1[OH:11])[S:4][CH2:3][CH2:2][S:1]2)=[O:17]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 119844811,4-dithiaspiro[4.5]decan-8-one

Product 1

HCID 59835936HCID 59835936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1,4-dithia-spiro[4.5]decan-8-one (2.35 g, 12.5 mmoL, 1.0 eq), in THF (10 mL) at 0° C. under nitrogen was added NaH (60%, 2.0 g, 50 mmoL, 4.0 eq) slowly. After gas releasing was completed, dimethy carbonate (11.3 g, 125 mmoL, 10.0 eq) was added via syringe. The reaction mixture was warmed to room temperature and further heated at 50° C. for 2 hours. The reaction was then cooled down to room temperature and quenched with saturated ammonia chloride solution. The solvent was removed in vacuo and the residue was partitioned between ethyl ether and water. The aqueous layer was extracted with ethyl ether twice. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give a colorless oil. The crude material was then purified by column chromatography using 5:1 hexanes: ethyl acetate to give the title compound as a colorless solid.

Workup

  1. temperaturefurther heated at 50° C. for 2 hours
  2. temperatureThe reaction was then cooled down to room temperature
  3. customquenched with saturated ammonia chloride solution
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between ethyl ether and water
  6. extractionThe aqueous layer was extracted with ethyl ether twice
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a colorless oil
  12. customThe crude material was then purified by column chromatography

Sources & evidence

ORD record
ord-014229e88fe047f088fb37233834d966
Source dataset
uspto-grants-2008_11
Patent number
US07452914B2

Reaction notes

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