Sodium Hydroxide → 2-(2-sulfanylethyl)pentanedioic Acid

HRID 1976715Notes

Reaction equation

HRID 1976715 reaction equation
[O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])[CH2:5][CH2:4][S:3]1.[OH-:14].[Na+]>C1COCC1>[SH:3][CH2:4][CH2:5][CH:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:2]([OH:1])=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11041823HCID 11041823, compound

Product 1

HCID 97941372-(2-sulfanylethyl)pentanedioic AcidYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(2-oxotetrahydro-3-thiophenyl)propanoate (0.77 g, 3.81 mmol) in THF (5 ml) was added sodium hydroxide (1 M in water, 5 ml). The mixture was allowed to stir for two days, then the THF was removed under reduced pressure, the aqueous layer was washed with ether, then acidified to pH 1 with HCl and extracted with ethyl acetate. The combined ethyl acetate extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography yielding a 150 mg of clear oil (20%). 1H NMR (d6-DMSO) δ 1.7 (m, 3H), 1.8 (m, 1H), 2.2 (m, 2H), 2.3-2.5 (m, 4H). Analysis calculated for C7H12SO4: C, 43.74; H, 6.29; S, 16.68. Found: C, 43.61; H, 6.39; S, 16.55.

Workup

  1. customthe THF was removed under reduced pressure
  2. washthe aqueous layer was washed with ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-35302182177c4a36a63d787a31f4e74f
Source dataset
uspto-grants-2001_05
Patent number
US06228888B1

Reaction notes

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