Acetylene → 2-Phenylbut-3-yn-1-ol

2-Phenyl-4-trimethylsilyl-but-3-yn-1-ol (Chem. Ber. (1988), 121, 1315-1320) (7.8 g) was dissolved in ethanol and the solution was cooled to -5° C. A solution of silver nitrate (8.9 g) in ethanol (60 ml) and water (21 ml) was added dropwise to the acetylene solution such that the temperature remained below 5° C. This precipitated the acetylene as the silver complex. A solution of potassium cyanide (17 g) in water (30 ml) was added dropwise to the stirred acetylene mixture and the resulting mixture was stirred at room temperature for 30 minutes. The mixture mainly dissolved and was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated. The residue was purified on silica using 10% ethyl acetate in hexane as eluant to afford the title compound (5 g) as a colourless oil.

1. customremained below 5° C
2. customThis precipitated the acetylene as the silver complex
3. additionA solution of potassium cyanide (17 g) in water (30 ml) was added dropwise to the stirred acetylene mixture
4. dissolutionThe mixture mainly dissolved
5. additionwas diluted with water
6. extractionextracted with ethyl acetate
7. washThe organic extracts were washed with brine
8. dry with materialdried (MgSO4)
9. customevaporated
10. customThe residue was purified on silica using 10% ethyl acetate in hexane as eluant

ORDレコード

ord-5b0feb349090451da9847168db764b49

出典データセット

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05728695