Water → HCID 18351761, compound
Reaction equation
C1CO[C:3]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH2:4][O:5][CH2:6][CH2:7][C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=3[O:10][CH:9]=2)[O:2]1.O>C1COCC1.Cl>[O:2]=[C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:4][O:5][CH2:6][CH2:7][C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=2[O:10][CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
3-(2-(2,2-ethylenedioxy-2-phenylethoxy)ethyl)-7-hydroxybenzofuran (185 mg) was dissolved in THF (3 ml). To this solution, one drop of concentrated hydrochloric acid was added and the solution was stirred at 50° C. for 29 hours, followed by refluxing the solution for 3 hours. The reaction solution was poured into water layer (30 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=2/1) using silica gel to obtain the desired compound (111 mg, yield: 69%).
Workup
- temperatureby refluxing the solution for 3 hours
- extractionextracted twice with ethyl acetate (20 ml)
- washwashed with saturated brine
- dry with materialby drying over sodium sulfate
- customAfter removing the sodium sulfate
- filtrationby filtration
- customthe solvent was removed under reduced pressure
- customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=2/1)
Sources & evidence
- ORD record
- ord-ad44c742d1094c0e94a27ea346c10f92
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06323235B1
Reaction notes
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