Sodium Bicarbonate → HCID 19096297, compound

HRID 486721Notes

Reaction equation

HRID 486721 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:12][S:11][CH:10]([CH2:13][CH2:14][O:15]C2CCCCO2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[C:1]([O:5][C:6]([CH:8]1[CH2:12][S:11][CH:10]([CH2:13][CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 54429164HCID 54429164, compound

Product 1

HCID 19096297HCID 19096297, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-tert-butoxycarbonyl-2-(2-tetrahydropyranyloxyethyl)tetrahydrothiophene (0.67 g) in methanol (20 ml), p-toluenesulfonic acid monohydrate (40 mg) was added and the mixture was stirred for 3 hours at room temperature. Saturated aqueous sodium bicarbonate solution was added to the mixture and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 470 mg (96%) of the titled compound (compound No. 2-1).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-ae2e0ca0a8cc47c2b51fce056311951f
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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