Potassium Hydroxide → 4'-Benzyloxyphenyl acetylene

温度

25 °C

4-benzyloxy iodobenzene (193 g, 0.625 mol), ethynyl-trimethyl-silane (75 g, 0.76 mol), Cul (2 g, 10.5 mmol) and Pd(PPh3)2Cl2 (1 g, 1.0 mmol) were added to diethylamine (880 mL) at 0° C. The reaction mixture was warmed to 25° C. and then stirred for 6 h. The reaction mixture was concentrated and partitioned in H2O/ethyl acetate (100 mL/100 mL). The reaction mixture was further extracted with ethyl acetate (300 mL×2). The combined organic layers were washed by water (300 mL), dried over MgSO4 and concentrated in vacuo. The crude product was dissolved in methanol (400 mL) and was stirred with KOH (28 g, 0.5 mol) for 1 h at 25° C. Concentration and purification by silica gel column chromatograph (5% ethyl acetate/Hexane) yielded 4-benzyloxy phenyl acetylene as liquid.

1. concentrationThe reaction mixture was concentrated
2. custompartitioned in H2O/ethyl acetate (100 mL/100 mL)
3. extractionThe reaction mixture was further extracted with ethyl acetate (300 mL×2)
4. washThe combined organic layers were washed by water (300 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. dissolutionThe crude product was dissolved in methanol (400 mL)
8. concentrationConcentration and purification by silica gel column chromatograph (5% ethyl acetate/Hexane)

ORDレコード

ord-7f0bafc984b14b18824e44153f5ddef6

出典データセット

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07183445B2