Hydrochloric Acid → HCID 11235827, compound

HRID 430793Notes

Reaction equation

HRID 430793 reaction equation
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[C:16](C)([O-:18])C.[K+].Br[CH2:22][CH2:23][C:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH:34]3[CH2:39]CCCO3)[C:27]=2[O:26][CH:25]=1.Cl.CN(C=[O:45])C>O>[C:9]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:8][CH2:22][CH2:23][C:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[C:32]([O:33][CH2:34][C:39]([O:18][CH3:16])=[O:45])[C:27]=3[O:26][CH:25]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 138160DiphenylmethanethiolHCID 18351690HCID 18351690, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11235827HCID 11235827, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diphenylmethanethiol (297 mg) was dissolved in DMF (2 ml) and potassium t-butoxide (166 mg) was added to the obtained solution, followed by stirring the resulting solution at room temperature for 5 minutes. To this reaction solution, a solution of 3-(2-bromoethyl)-7-tetrahydropyranyloxybenzofuran (335 mg) in DMF (2.5 ml) was added dropwise for 5 minutes, and the resulting solution was stirred at room temperature for 15 minutes. To this reaction solution, 1N hydrochloric acid (1.5 ml) was added and the solution was stirred at room temperature for 1 hour. The reaction mixture was poured into water layer (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the obtained residue was dissolved in DMF (4 ml). To this solution, potassium carbonate (205 mg) and methyl bromoacetate (0.19 ml) were added and the resulting mixture was stirred at room temperature for 3.5 hours. The reaction solution was poured into water layer (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated saline, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (255 mg, yield: 60%).

Workup

  1. stirringthe resulting solution was stirred at room temperature for 15 minutes
  2. stirringthe solution was stirred at room temperature for 1 hour
  3. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  4. washwashed with saturated brine
  5. dry with materialby drying over sodium sulfate
  6. customAfter removing the sodium sulfate
  7. filtrationby filtration
  8. customthe solvent was removed under reduced pressure
  9. dissolutionthe obtained residue was dissolved in DMF (4 ml)
  10. additionTo this solution, potassium carbonate (205 mg) and methyl bromoacetate (0.19 ml) were added
  11. stirringthe resulting mixture was stirred at room temperature for 3.5 hours
  12. additionThe reaction solution was poured into water layer (50 ml)
  13. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  14. washwashed with saturated saline
  15. dry with materialby drying over sodium sulfate
  16. customAfter removing the sodium sulfate
  17. filtrationby filtration
  18. customthe solvent was removed under reduced pressure
  19. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-973a8d6046e44f09ad25b2496c98b001
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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