تفاعل #5750

ord-80a36a4efaf343448d7ae9f9feb6eb02

معادلة التفاعل

O
water
c1c[nH]cn1
imidazole
CC(C)(C)[Si](C)(C)Cl
chlorodimethyl t-butylsilane
CC(=O)OCC=C(C)CCC=C(C)CO
8-Acetoxy-2,6-dimethyl-2,6-octadien-1-ol
CC(=O)OCC=C(C)CCC=C(C)CO[Si](C)(C)C(C)(C)C
1-acetoxy-8-(dimethyl t-butylsilyl)oxy-3,7-dimethyl-2,6-octadiene
المردود 75.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصthe product was extracted with hexane (20 m1×2)
  2. 2
    تجفيفThe extract was dried over MgSO4
  3. 3
    أخرىevaporated in vacuo
  4. 4
    أخرىto remove the solvent
  5. 5
    أخرىto give a residue, which

الإجراء التجريبي

8-Acetoxy-2,6-dimethyl-2,6-octadien-1-ol in dimethylformamide (4 ml) was stirred on an ice bath. To the solution were added imidazole (338 mg, 4.96 mmol) and chlorodimethyl t-butylsilane (410 mg, 2.73 mmol), and the mixture was stirred at room temperature for one hour. After addition of water (30 ml) to the reaction mixture, the product was extracted with hexane (20 m1×2). The extract was dried over MgSO4 and evaporated in vacuo to remove the solvent to give a residue, which was subjected to silica gel column chromatography to obtain 1-acetoxy-8-(dimethyl t-butylsilyl)oxy-3,7-dimethyl-2,6-octadiene (606 mg, 75%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05245085uspto-grants-1993_09