تفاعل #487518

ord-c181300b85774c64a75f7795a498911c

معادلة التفاعل

O=c1ccc2ccc(O)cc2o1
7-hydroxycoumarin
[H-].[Na+]
NaH
C=CCCBr
4-bromo-1-butene
C=CCCOc1ccc2ccc(=O)oc2c1
4-(7-coumarinyloxy)-1-butene
المردود 67.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
60°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    غسيلis washed with water (3×300 mL)
  2. 2
    أخرىThe residue is chromatographed with the mixture (ethyl acetate-hexane)

الإجراء التجريبي

A suspension of 7-hydroxycoumarin (3 g, 19.6 mmol) in DMF (20 ml) is treated with NaH (60% suspension in oil, 1.03 g, 25.9 mmol), then with 4-bromo-1-butene (2.65 g, 19.6 mmol). It is heated to 60° C. for 24 hours, then it is diluted with ethyl acetate (400 ml), and it is washed with water (3×300 mL) then with 1 M NaOH (3×200 ml). The residue is chromatographed with the mixture (ethyl acetate-hexane) to obtain 4-(7-coumarinyloxy)-1-butene (2.7 g, 67%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08741593B2uspto-grants-2014_06