Hydrochloric Acid → HCID 18351822, compound

HRID 430772Notes

Reaction equation

HRID 430772 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Cl[CH2:24][C:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[C:33]([O:34][CH3:35])[C:28]=2[O:27][CH:26]=1.Cl>CN(C=O)C.O>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][O:10][CH2:24][C:25]2[C:29]3[CH:30]=[CH:31][CH:32]=[C:33]([O:34][CH3:35])[C:28]=3[O:27][CH:26]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 299083,3-DiphenylpropanolHCID 18351661HCID 18351661, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18351822HCID 18351822, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

3,3-diphenyl-1-propanol (550 mg) was dissolved in DMF (5 ml) and the obtained solution was cooled to 0° C. To this solution, potassium t-butoxide (291 mg) was added and the solution was stirred at 0° C. for 10 minutes. To the reaction solution, 3-chloromethyl-7-methoxybenzofuran (339 mg) solution in DMF (4 ml) was added dropwise and the resulting solution was stirred at 0° C. for 30 minutes. After neutralizing the reaction solution with 1N hydrochloric acid, the solution was poured into water layer (50 ml) and 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 residue was purified by column chromatography (solvent: hexane/ethyl acetate=9/1) using silica gel to obtain the desired compound (547 mg, yield: 85%).

Workup

  1. stirringthe resulting solution was stirred at 0° C. for 30 minutes
  2. extractionextracted twice with ethyl acetate (20 ml)
  3. washwashed with saturated brine
  4. dry with materialby drying over sodium sulfate
  5. customAfter removing the sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-ba5a23c38e384bde8f3136b741204946
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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