Hydrochloric Acid → HCID 18351764, compound

HRID 430782Notes

Reaction equation

HRID 430782 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15]C3CCCCO3)[C:9]=2[O:8][CH:7]=1.Br[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>CN(C=O)C.O>[C:26]1([CH2:25][CH2:24][CH2:23][O:3][CH2:4][CH2:5][C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[C:14]([OH:15])[C:9]=3[O:8][CH:7]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 18351843HCID 18351843, compound

Product 1

HCID 18351764HCID 18351764, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60%, 27 mg) was suspended in DMF (1 ml) and the obtained suspension was cooled to 0° C. To this solution, a solution of 3-(2-hydroxyethyl)-7-tetrahydropyranyloxybenzofuran (118 mg) in DMF (0.5 ml) was added dropwise and the obtained mixture was stirred at 0° C. for 10 minutes. To this solution, 1-bromo-3-phenyl-propane (0.27 ml) was added and the solution was stirred at 0° C. for 1 hour and then at room temperature for 45 hours. A catalytic amount of concentrated hydrochloric acid was added to the reaction solution and the solution was stirred for 2 hours. The reaction solution was poured into water layer (30 ml) and the resultant was extracted twice with ethyl acetate (15 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 residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (106 mg, yield: 80%).

Workup

  1. stirringthe solution was stirred at 0° C. for 1 hour
  2. waitat room temperature for 45 hours
  3. stirringthe solution was stirred for 2 hours
  4. extractionthe resultant was extracted twice with ethyl acetate (15 ml)
  5. washwashed with saturated brine
  6. dry with materialby drying over sodium sulfate
  7. customAfter removing the sodium sulfate
  8. filtrationby filtration
  9. customthe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-34308594c86d4d7faa226b1d9e40a6ac
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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