تفاعل #1702037

ord-e196bd1b8d46431894e5c444898e7d67

معادلة التفاعل

[Cl-].[Na+]
sodium chloride
OCCOCCCl
2-(2-chloroethoxy)ethanol
[N-]=[N+]=[N-].[Na+]
sodium azide
[N-]=[N+]=NCCOCCO
desired product
المردود 69.0%
[N-]=[N+]=NCCOCCO
2-(2-Azidoethoxy)ethanol
المردود 69.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
80°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصextracted with 3×50 mL of ether
  2. 2
    تجفيفThe combined organics were dried over anhydrous sodium sulfate
  3. 3
    ترشيحfiltered
  4. 4
    تركيزconcentrated

الإجراء التجريبي

A solution of 10.0 grams of 2-(2-chloroethoxy)ethanol in 50 mL of deionized water was treated with 10.4 grams (2 eq) of sodium azide, and the reaction mixture was heated at 80° C. for 48 hours. The solution was cooled to room temperature, saturated with sodium chloride and extracted with 3×50 mL of ether. The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated to give 7.25 grams (69%) of the desired product as a clear, colorless oil. 1H NMR (400 MHz, CDCl3): δ=2.05 (t, J=6.4 Hz, 1H, OH), 3.42 (t, J=5 Hz, 2H), 3.63 (dd, J=4.4, 5.6 Hz), 3.71 (dd, J=4.4, 4.8 Hz, 2H), 3.77 (dt, J=4.4, 6 Hz, 2H).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08765432B2uspto-grants-2014_07