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1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: 1-chloro-2-(2-hydroxyphenyl)-hexan-2-ol With butyl magnesium bromide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 70℃; for 0.166667h; | 100% |
2-(hex-1-yn-1-yl)phenol
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: 2-(hex-1-yn-1-yl)phenol With N,N,N,N,-tetramethylethylenediamine; diethylzinc In toluene at 120℃; for 1h; Stage #2: With ammonium chloride In toluene | 99% |
Stage #1: 2-(hex-1-yn-1-yl)phenol With n-butyllithium In diethyl ether; hexane at 0 - 20℃; for 30h; Stage #2: With zinc(II) chloride In toluene at 120℃; for 1h; Stage #3: With ammonium chloride In water; toluene | 98% |
With caesium carbonate; copper(l) chloride In acetonitrile at 20℃; under 760.051 Torr; for 6h; | 91.8% |
Conditions | Yield |
---|---|
With copper(l) iodide; tetra-(n-butyl)ammonium iodide; potassium carbonate; palladium In toluene at 40℃; Reagent/catalyst; Temperature; Sonogashira Cross-Coupling; Inert atmosphere; | 96.6% |
With potassium carbonate at 60℃; for 1h; | 91% |
With copper(l) iodide; L-proline; sodium hydroxide In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere; Sealed tube; | 85% |
2-phenoxyhexanal
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With Amberlyst 15 In benzene Heating; | 94% |
With acetic acid; zinc(II) chloride for 0.166667h; Heating; | 24% |
n-butyl magnesium bromide
2-(methylsulfanyl)benzofuran
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride In tetrahydrofuran at 25℃; for 0.5h; Schlenk technique; Inert atmosphere; | 94% |
2-(2-formyl-phenoxy)-hexanoic acid
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
Stage #1: 2-(2-formyl-phenoxy)-hexanoic acid With triethylamine; p-toluenesulfonyl chloride In toluene at 70 - 80℃; for 2h; Stage #2: With sodium hydroxide In water; toluene at 70 - 75℃; for 2h; | 90% |
With sodium acetate; acetic anhydride at 90 - 100℃; Temperature; Reagent/catalyst; Large scale; | 73.1% |
With sodium acetate; acetic anhydride In acetic acid for 8h; Heating; | 64% |
With sodium acetate; acetic anhydride; acetic acid Heating; |
1-hexynyl-2-(methoxymethoxy)benzene
1,3-Dimethoxybenzene
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With gold(III) chloride; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 18h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With cyclopentene In toluene at 100℃; for 10h; Inert atmosphere; regioselective reaction; | 85% |
2-n-butylbenzo[b]furan
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 105℃; for 22h; | 82% |
Conditions | Yield |
---|---|
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 1-bromo-butane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 82% |
Stage #1: 1-benzofurane With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: 1-bromo-butane In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 30% |