Triethylamine → HCID 15462826, compound

HRID 1357195Notes

Reaction equation

HRID 1357195 reaction equation
CCN(CC)CC.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]1[C:22]1[O:27][C:26](=[O:28])[C:25]([CH3:29])=[C:24]([OH:30])[C:23]=1[CH3:31].OS([O-])(=O)=O.[K+]>C1COCC1>[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]1[C:22]1[O:27][C:26](=[O:28])[C:25]([CH3:29])=[C:24]([O:30][S:9]([CH3:8])(=[O:11])=[O:10])[C:23]=1[CH3:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516920Potassium bisulfateHCID 54712960HCID 54712960, compound

Product 1

HCID 15462826HCID 15462826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Et3N (130 μl) and methanesulfonyl chloride (24 μl) were added to a suspension of 6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one (40 mg) in THF (5 ml), and the mixture was stirred at room temperature for one hour. The reaction solution was poured into aqueous KHSO4 and extracted with AcOEt, and the organic layer was rinsed with saturated saline and dried with MgSO4, and then filtered and concentrated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1) to obtain 6-(benzofuran-2-yl)-3,5-dimethyl-4-methanesulfonyloxy-2H-pyran-2-one.

Workup

  1. extractionextracted with AcOEt
  2. washthe organic layer was rinsed with saturated saline
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1)

Sources & evidence

ORD record
ord-fe5d60476f6f45aea79025ab4b93aa25
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

Loading…