تفاعل #54943

ord-689e2f5deb7742b2b55bcd01eb67d1b2

معادلة التفاعل

CCN(CC)CC
triethylamine
C#CCC(C)(O)C#CCC
4-methyl-1,5-octadiyn-4(RS)-ol
CC[Si](Cl)(CC)CC
triethylsilyl chloride
CN(C)C=O
dimethylformamide
C#CCC(C)(C#CCC)O[Si](CC)(CC)CC
4-methyl-1,5-octadiyn-4(RS)-ol triethylsilyl ether

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe layers were separated
  2. 2
    غسيلthe organic layer was washed successively with dilute hydrochloric acid, water and saturated aqueous potassium bicarbonate
  3. 3
    تجفيفdried over anhydrous sodium sulfate
  4. 4
    أخرىthe solvent was removed under reduced pressure
  5. 5
    غسيلAdsorption of the residue on a silica gel chromatographic column followed by elution with hexane

الإجراء التجريبي

A mixture consisting of 1.25 parts of 4-methyl-1,5-octadiyn-4(RS)-ol, 1.5 parts of triethylsilyl chloride, 2.5 parts by volume of dimethylformamide and 1 part by volume of triethylamine was stirred in an atmosphere of nitrogen at room temperature for about 24 hours. The mixture was then poured into benzene and diluted with water. The layers were separated and the organic layer was washed successively with dilute hydrochloric acid, water and saturated aqueous potassium bicarbonate, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. Adsorption of the residue on a silica gel chromatographic column followed by elution with hexane afforded 4-methyl-1,5-octadiyn-4(RS)-ol triethylsilyl ether.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04151187uspto-grants-1979_04