Hydrochloric Acid → HCID 54165423, compound

HRID 486733Notes

Reaction equation

HRID 486733 reaction equation
[SH:1][CH2:2][C@H:3]1[CH2:8][C@@H:7]([CH2:9][SH:10])[O:6][C:4]1=[O:5].Cl>C1COCC1.[OH-].[Na+]>[C:4]([C@@H:3]1[CH2:2][S:1][C@@H:7]([CH2:9][SH:10])[CH2:8]1)([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86747636HCID 86747636, compound

Product 1

HCID 54165423HCID 54165423, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of cis-2,4-bis(mercaptomethyl)-4-butanolide (600 mg) in THF (20 ml), 1N sodium hydroxide solution (3.4 ml) was added and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude trans-4-carboxy-2-mercaptomethyltetrahydrothiophene.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8e3a5b7d1ee4ff09933cc09850ec3e8
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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