2-Naphthalenethiol → 2-Methoxycarbonylmethyl-3-(2-naphthylthio)propionic acid

HRID 1645784Notes

Reaction equation

HRID 1645784 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[SH:11].[CH3:12][O:13][C:14]([CH2:16][C:17](=[CH2:21])[C:18]([O-:20])=[O:19])=[O:15].[Na+]>CO>[CH3:12][O:13][C:14]([CH2:16][CH:17]([CH2:21][S:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:18]([OH:20])=[O:19])=[O:15]

Participants

4

Reactant 2

HCID 70582-NaphthalenethiolHCID 23678954Sodium 3-methoxycarbonyl-2-methylenepropionate

Product 1

HCID 198023292-Methoxycarbonylmethyl-3-(2-naphthylthio)propionic acidYield 53.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 2-naphthalenethiol (0.38 g), sodium 3-methoxycarbonyl-2-methylenepropionate (0.39 g), methanol (20 ml), and triton B (40% methanol solution, 10 drops) was refluxed for 12 hours. The reaction mixture was concentrated in vacuo, and the resulting residue was acidified with a dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried over MgSO4. The solvent was evaporated at reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica eluting with chloroform/methanol (20:1), and recrystallized from isopropyl ether to give 0.38 g of 2-methoxycarbonylmethyl-3-(2-naphthylthio)propionic acid.

Workup

  1. temperaturewas refluxed for 12 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated at reduced pressure
  7. customthe residue was purified by medium pressure liquid column chromatography on silica eluting with chloroform/methanol (20:1)
  8. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-5efc2806d72d499e81fc47ce783f8fac
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

Loading…