Hydrochloric Acid → 6,7-Dihydroxy-4-thiaoctanoic acid methyl ester

HRID 1720803Notes

Reaction equation

HRID 1720803 reaction equation
[O:1]1[CH2:6][CH:2]1[CH:3]([OH:5])[CH3:4].Cl.[SH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]>C(Cl)Cl.C[O-].[Na+]>[CH3:14][O:13][C:11](=[O:12])[CH2:10][CH2:9][S:8][CH2:6][CH:2]([OH:1])[CH:3]([OH:5])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 18050Methyl 3-mercaptopropionateHCID 115934311-(Oxiran-2-yl)ethan-1-ol

Product 1

HCID 106798886,7-Dihydroxy-4-thiaoctanoic acid methyl esterYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10942334Sodium MethoxideSolvent

Procedure

To a solution of 3,4-epoxy-2-butanol as obtained in Reference Example 43 (1.13 g) in methylene chloride (4 ml), methyl 3-mercaptopropionate (2.00 ml) and sodium methylate (260 μl) were added under ice cooling conditions, followed by stirring at room temperature for 1 day. To the reaction mixture, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate; the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1) to yield the title compound (1.47 g, yield 55%) as a colorless oily substance.

Workup

  1. additionwere added under ice cooling conditions
  2. extractionthe mixture was extracted with ethyl acetate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-5de6a0153ba54a78b04b9d334bd4a2b7
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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