Triethylamine → HCID 11290118, compound

HRID 2417266Notes

Reaction equation

HRID 2417266 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.[SH:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([S:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131740Ethyl bromo(4-methoxyphenyl)acetateHCID 2401474-Mercaptophenol

Product 1

HCID 11290118HCID 11290118, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl bromo(4-methoxyphenyl)acetate (16.5 g, 60.4 mmol) was added to a stirring solution of triethyl amine (10 ml), and 4-mercaptophenol (7.63 g, 60.4 mmol) in Chloroform (200 ml). The mixture was heated at reflux overnight before it was concentrated and the residue was extracted in ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The compound was isolated using silica-gel column chromatography by eluting it with 20% ethyl acetate: hexane solution. Ethyl[(4-hydroxyphenyl)sulfanyl](4-methoxyphenyl)acetate was isolated as a yellow oil (15.82 g). Yield 82%; MS: 317.2 (M−H)−

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight before it
  3. concentrationwas concentrated
  4. extractionthe residue was extracted in ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe compound was isolated
  10. washby eluting it with 20% ethyl acetate

Sources & evidence

ORD record
ord-1389c9241ecd4be187f283883995ae73
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

Loading…