Methanol → HCID 68425140, compound

HRID 1927449Notes

Reaction equation

HRID 1927449 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[SH:16].[CH3:17]O>>[CH3:17][O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:7]([Br:6])=[C:8]([SH:16])[CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 68425075HCID 68425075, compound

Product 1

HCID 68425140HCID 68425140, compound

Procedure

Conc. H2SO4 (6.25 mL) was added dropwise to a refluxing solution of Example 1b and its dimer (3 g) in dry MeOH (60 mL). The reaction mixture was refluxed for 15 h, concentrated and treated with ice to obtain a mixture of the desired ester and that of its dimer, which was filtered, washed with water and dried. Purification was effected using flash chromatography (silica gel, EtOAc/PE60-80° C.) to obtain the title compound and its dimer ester (2.8 g) which was in turn converted into the title compound as given below: Triphenylphosphine (1.5 g, 5.71 mmol) was added to a solution of the dimer ester in MeOH/H2O (15 mL 4:1, v/v) and allowed to stir overnight at room temperature. The reaction mixture was concentrated, treated with water and extracted with ethyl acetate. The ethyl acetate layer was concentrated and the crude obtained was purified using flash chromatography as above to obtain more of the title compound. Yield: 2.0 g, (72%); mp: 81° C.; 1H NMR (CDCl3): δ 3.90 (s, 3H, OCH3), 4.0 (s, 1H, SH), 7.05-7.25 (m, 3H, Ar); MS: m/e (EI+) 247 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. concentrationconcentrated
  3. additiontreated with ice
  4. customto obtain
  5. filtrationthat of its dimer, which was filtered
  6. washwashed with water
  7. customdried
  8. customPurification
  9. customflash chromatography (silica gel, EtOAc/PE60-80° C.)

Sources & evidence

ORD record
ord-474f5a830741445f95ba2924982670b6
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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