Triethylamine → HCID 66926177, compound

HRID 2170797Notes

Reaction equation

HRID 2170797 reaction equation
O[CH:2]([CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[CH:3]1[C:7](=[O:8])[CH:6]=[C:5]([O:9][CH3:10])[CH2:4]1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:10][O:9][C:5]1[CH2:4][C:3](=[CH:2][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:7](=[O:8])[CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 66926131HCID 66926131, compound

Product 1

HCID 66926177HCID 66926177, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[hydroxy-(tetrahydro-pyran-4-yl)-methyl]-3-methoxy-cyclopent-2-enone (1.1 g, 5 mmol) was dissolved in dichloromethane (25 ml) in a 50 ml round bottom flask fitted with a reflux condenser. Triethylamine (1.4 ml, 10 mmol) and then methane sulfonyl chloride (0.8 ml, 10 mmol) was added dropwise which caused the reaction to warm to reflux. After 10 minutes the reaction was quenched by the addition of 1 M hydrochloric acid (10 ml). The layers were separated and the organics collected, passed through a phase separation cartridge and the solvent removed in vacuo. The crude product was dissolved in methanol (25 ml) and anhydrous potassium carbonate (1.4 g, 10 mmol) added and the mixture was stirred at room temperature for 72 h. The solvent was then removed in vacuo and the residue dissolved in ethyl acetate (25 ml) and filtered to remove any solid. The filtrate was evaporated to dryness and the residue purified on by column chromatography (Hexane/EtOAc (7:3) to 100% EtOAc) to give 3-methoxy-5-[1-(tetrahydro-pyran-4-yl)-methylidene]-cyclopent-2-enone (938 mg).

Workup

  1. customfitted with a reflux condenser
  2. customthe reaction
  3. temperatureto warm to reflux
  4. customAfter 10 minutes the reaction was quenched by the addition of 1 M hydrochloric acid (10 ml)
  5. customThe layers were separated
  6. customthe organics collected, passed through a phase separation cartridge
  7. customthe solvent removed in vacuo
  8. dissolutionThe crude product was dissolved in methanol (25 ml)
  9. customThe solvent was then removed in vacuo
  10. dissolutionthe residue dissolved in ethyl acetate (25 ml)
  11. filtrationfiltered
  12. customto remove any solid
  13. customThe filtrate was evaporated to dryness
  14. customthe residue purified on by column chromatography (Hexane/EtOAc (7:3) to 100% EtOAc)

Sources & evidence

ORD record
ord-914bb658f34d43109e4c03d490216163
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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