تفاعل #1121720

ord-8a6e53357f4644599400ba263895f79e

معادلة التفاعل

CCN(CC)CC
triethylamine
COc1ccc(C(=O)Cl)cc1
4-methoxybenzoyl chloride
CN1CCN(C)C1=O
1,3-dimethyl-2-imidazolidinone
CC(=O)c1ccc(C(C)(C)C)cc1
4-tert-butylacetophenone
C=C(OC(=O)c1ccc(OC)cc1)c1ccc(C(C)(C)C)cc1
uncolored oil
المردود 7.0%
C=C(OC(=O)c1ccc(OC)cc1)c1ccc(C(C)(C)C)cc1
1-(4-Tert-butylphenyl)-vinyl 4-methoxybenzoate
المردود 7.0%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe first collected fraction was purified twice by flash chromatography (hexane/dichloromethane 3:2 and next, hexane/dichloromethane 4:1)

الإجراء التجريبي

4-methoxybenzoyl chloride (2.35 g, 13.8 mmol), 0.65 g of cuprous chloride and 5.6 mL of 1,3-dimethyl-2-imidazolidinone were added to crude 4-tert-butylacetophenone trimethylsilylenol (6.7 mmol). After stirring the solution for 20 hours at room temperature, 1.4 mL of triethylamine and 10 mL of chloroform were added. Then the solution was chromatographied through flash silica column (hexane/ethyl acetate 10:1). The first collected fraction was purified twice by flash chromatography (hexane/dichloromethane 3:2 and next, hexane/dichloromethane 4:1) giving 0.14 g of an uncolored oil corresponding to 1-(4-tert-butylphenyl)-vinyl 4-methoxybenzoate. Yield 7%.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08545816B2uspto-grants-2013_10