Hydrochloric Acid → 3-[2-[2-Phenylethoxy]ethylthio]propanoic acid

HRID 265296

Reaction equation

HRID 265296 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][SH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:16][CH2:17][C:18]([OH:20])=[O:19].Cl>CN(C=O)C.O>[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][S:12][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 115533-Bromopropionic acidHCID 24758Sodium hydrideHCID 187790402-(2-Phenylethoxy)ethane-1-thiol

Product 1

HCID 190822633-[2-[2-Phenylethoxy]ethylthio]propanoic acidYield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2-[2-phenylethoxy]ethane thiol (2.13 g) in dry DMF (10 ml) was added dropwise to a cooled (0°) stirred suspension of sodium hydride (0.60 g, 80% in oil) in DMF (50 ml). The mixture was stirred at 0° for 90 min. A solution of 3-bromopropanoic acid (3.15 g) in dry DMF (10 ml) was then added dropwise and the reaction was stirred at room temperature for 16 hours. Water (250 ml) was added and the whole was acidified to pH 2/3 with concentrated hydrochloric acid. The aqueous solution was extracted several times with ether and the combined ethereal layers were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. This yielded the crude acid which was purified by flash chromatography over silica using 6:1 dichloromethane:ether (1 drop acetic acid/100 ml of eluant) to give the subtitled compound (2.15 g).

Workup

  1. temperaturea cooled (0°)
  2. stirringThe mixture was stirred at 0° for 90 min
  3. stirringthe reaction was stirred at room temperature for 16 hours
  4. extractionThe aqueous solution was extracted several times with ether
  5. washthe combined ethereal layers were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThis yielded the crude acid which
  9. customwas purified by flash chromatography over silica using 6:1 dichloromethane

Sources & evidence

ORD record
ord-045f6311451245aeab0e5fac0928da69
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Linked notes

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