Hydrochloric Acid → 1,4-Anhydro-2,5-dideoxy-2-(methoxycarbonyl)-1-thiopent-3-ulose

HRID 595066Notes

Reaction equation

HRID 595066 reaction equation
C(O[C:4](=[O:14])[CH:5]([S:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH3:6])C.C[O-].[Na+].Cl>CO>[CH3:6][CH:5]1[S:7][CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[C:4]1=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 20472469Ethyl 2-[(3-methoxy-3-oxopropyl)sulfanyl]propanoate

Product 1

HCID 126586981,4-Anhydro-2,5-dideoxy-2-(methoxycarbonyl)-1-thiopent-3-uloseYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(2-ethoxy-1-methyl-2-oxo-ethyl)sulfanylpropanoate (2.2 g, 10 mmol) in methanol (15 mL) at 0° C. was added sodium methoxide (886 mg, 16.4 mmol). The reaction was warmed to rt and stirred for 3 h. The mixture was acidified with 1 N HCl to pH 2 and extracted with DCM. The organic phase was washed with water and brine, dried (Na2SO4), concentrated and purified by column chromatography, eluting with EtOAc in petroleum (3%-10%) to give methyl tetrahydro-5-methyl-4-oxothiophene-3-carboxylate as a colourless oil (0.85 g, 50% yield).

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by column chromatography
  6. washeluting with EtOAc in petroleum (3%-10%)

Sources & evidence

ORD record
ord-cc00fb1b042c4d248b89fc855f5102f8
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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