Potassium Carbonate → HCID 22273513, compound

HRID 2375290Notes

Reaction equation

HRID 2375290 reaction equation
C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:12][CH2:13][CH2:14][O:15][CH3:16])(=O)=O.[Br:17][C:18]1[CH:23]=[CH:22][C:21](S)=[CH:20][CH:19]=1.O[O:26][S:27]([O-:29])=O.[K+]>CN(C=O)C.O>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][S:27]([C:21]1[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][CH:20]=1)(=[O:29])=[O:26]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 116939633-Methoxypropyl methanesulfonateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22273513HCID 22273513, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Potassium carbonate (2.8 g, 20 mmol) was added to a solution of 3-methoxypropan-1-yl methansulphonate (Method 68; 3.25 g, 19.3 mmol) and 4-bromothiophenol (3.48 g, 18.4 mmol) in DMF (30 ml) and the mixture heated at 40° C. for 4 hours. The mixture was allowed to cool to ambient temperature, poured into water (100 ml) and extracted with EtOAc (2×50 ml). The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml), dried (Chemelut column CE1010) and the volatiles removed by evaporation. The residue was dissolved in MeOH (150 ml) and water (30 ml) and oxone (13.4 g, 21.6 mmol) was added in portions. The mixture was stirred at ambient temperature for 18 hours. The MeOH was evaporated, water (50 ml) added and the solution extracted with DCM (3×50 ml). The extracts were combined, washed with brine (50 ml), dried (Chemelut column CE1010), and evaporated. The residue was purified by flash chromatography on silica gel eluting with iso-hexane: EtOAc (100:0 increasing in polarity to 90:10) to give the title compound (3.32 g, 62%) as a colourless oil. NMR 1.95 (m, 2H), 3.19 (m, 2H), 3.26 (s, 3H), 3.41 (t, 2H), 7.70 (d, 2H), 7.78 (d, 2H).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with EtOAc (2×50 ml)
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml)
  4. dry with materialdried (Chemelut column CE1010)
  5. customthe volatiles removed by evaporation
  6. dissolutionThe residue was dissolved in MeOH (150 ml)
  7. customThe MeOH was evaporated
  8. additionwater (50 ml) added
  9. extractionthe solution extracted with DCM (3×50 ml)
  10. washwashed with brine (50 ml)
  11. dry with materialdried (Chemelut column CE1010)
  12. customevaporated
  13. customThe residue was purified by flash chromatography on silica gel eluting with iso-hexane: EtOAc (100:0 increasing in polarity to 90:10)

Sources & evidence

ORD record
ord-0c2d5f05652446ce803a54d6d5ede578
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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