Ethyl 3,6-dihydro-5-mercapto-2H-pyran-4-carboxylate → HCID 22026130, compound

HRID 2220195Notes

Reaction equation

HRID 2220195 reaction equation
B1([O-])OO1.[OH2:5].[OH2:6].[OH2:7].O.[Na+].[SH:10][C:11]1[CH2:16][O:15][CH2:14][CH2:13][C:12]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)(=O)C>[CH2:20]([O:19][C:17]([C:12]1[CH2:13][CH2:14][O:15][CH2:16][C:11]=1[S:10]([OH:7])(=[O:6])=[O:5])=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 22026123Ethyl 3,6-dihydro-5-mercapto-2H-pyran-4-carboxylateHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 22026130HCID 22026130, compoundYield 219.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
52.5 °C

Procedure

Sodium perborate tetrahydrate (24.5 g) was added to acetic acid (130 ml) and the mixture was heated to 50-55° C. Thereto was added dropwise a solution of ethyl 5-sulfanyl-3,6-dihydro-2H-pyran-4-carboxylate (10.0 g) in acetic acid (30 ml) over 2 h. The mixture was stirred at 50-55° C. for 3 h, and the reaction mixture was concentrated under reduced pressure. To the residue was added acetonitrile (230 ml) and the mixture was stirred at room temperature for 2 days, and the resultant insoluble material was removed off by filtration and washed with acetonitrile (70 ml). The filtrate and washing were combined and the mixture was concentrated under reduced pressure. The residue was dissolved in acetonitrile (160 ml) and the mixture was stirred at room temperature for 6 h. The obtained insoluble material was removed off by filtration, and the filtrate was concentrated under reduced pressure. To the residue was added diisopropyl ether (100 ml), and the precipitated insoluble material was filtered off to give 4-(ethoxycarbonyl)-5,6-dihydro-2H-pyran-3-sulfonic acid as a pale-yellow oil (27.6 g) containing an inorganic product.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added acetonitrile (230 ml)
  3. stirringthe mixture was stirred at room temperature for 2 days
  4. customthe resultant insoluble material was removed off by filtration
  5. washwashed with acetonitrile (70 ml)
  6. washThe filtrate and washing
  7. concentrationthe mixture was concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in acetonitrile (160 ml)
  9. stirringthe mixture was stirred at room temperature for 6 h
  10. customThe obtained insoluble material was removed off by filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. additionTo the residue was added diisopropyl ether (100 ml)
  13. filtrationthe precipitated insoluble material was filtered off

Sources & evidence

ORD record
ord-a11e50c04a4c47688f9fba3f0dc826cc
Source dataset
uspto-grants-2008_08
Patent number
US07417059B2

Reaction notes

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