Sodium Bicarbonate → Ethyl 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)acetate

HRID 1417483Notes

Reaction equation

HRID 1417483 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH2:17][CH2:18][CH:19]([CH2:21][C:22]3[O:23][CH2:24][C:25](C)(C)N=3)[S:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[OH:30].[Na+]>S(=O)(=O)(O)O.C(O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH2:17][CH2:18][CH:19]([CH2:21][C:22]([O:23][CH2:24][CH3:25])=[O:30])[S:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 57015605HCID 57015605, compound

Product 1

HCID 53821095Ethyl 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

60 mg of 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)methyl-4,4-dimethyl-2-oxazoline (prepared as described in Example 81) was dissolved in 5% v/v sulfuric acid in ethanol, and the mixture was refluxed for 6 hours. After this time, the reaction mixture was neutralized by the addition of a saturated aqueous solution of sodium hydrogencarbonate and then extracted with ethyl acetate. The ethyl acetate fraction was then washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a mixture of 20% v/v ethyl acetate in hexane as the eluent, to afford 46 mg of the title compound as an oil.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate fraction was then washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by evaporation under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography
  7. additiona mixture of 20% v/v ethyl acetate in hexane as the eluent

Sources & evidence

ORD record
ord-189730aed94544008687704c460bcd28
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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