تفاعل #1605818

ord-b99669a7b4c243d8a5ccdf71818e465a

معادلة التفاعل

CC(C)(C)[Si](C)(C)Cl
tert-butyldimethylchlorosilane
O=[N+]([O-])c1cc(OCCCCCCCCO)ccc1-c1ccccc1
8-(3-Nitro-4-phenylphenoxy)octan-1-ol
c1c[nH]cn1
imidazole
CC(C)(C)[Si](C)(C)OCCCCCCCCOc1ccc(-c2ccccc2)c([N+](=O)[O-])c1
tert-butyldimethyl{[8-(3-nitro-4-phenylphenoxy)octyl]oxy}silane
المردود 86.1%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىpurified water
  2. 2
    workup.ADDITIONwas added
  3. 3
    أخرىthe reaction
  4. 4
    استخلاصthe mixture was extracted with ethyl acetate
  5. 5
    غسيلThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  6. 6
    تجفيفa saturated aqueous solution of ammonium chloride, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  7. 7
    تركيزconcentrated under reduced pressure
  8. 8
    أخرىThe residue was purified by flash column chromatography

الإجراء التجريبي

8-(3-Nitro-4-phenylphenoxy)octan-1-ol (1.23 g, 3.5 mmol) and imidazole (408 mg, 6.0 mmol) were dissolved in tetrahydrofuran (15 mL) and a solution of tert-butyldimethylchlorosilane (750 mg, 5.0 mmol) in tetrahydrofuran (5 mL) was added thereto. After stirring the reaction mixture at room temperature for 18 hours, purified water was added to stop the reaction and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain tert-butyldimethyl{[8-(3-nitro-4-phenylphenoxy)octyl]oxy}silane (1.38 g).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09072734B2uspto-grants-2015_07