تفاعل #91599

معادلة التفاعل

(cyclohexylmethyl)bromide

5-bromofuran-2-carboxylic acid

(cyclohexylmethyl)bromide

K2CO3

→

cyclohexylmethyl 5-bromofuran-2-carboxylate

المذيبات

NMP

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   تركيزthe reaction mixture was concentrated under reduced pressure
3. 3
   أخرىThe residue was partitioned between aqueous NaHCO3 (10%) and hexanes
4. 4
   استخلاصaqueous layer was extracted with hexanes
5. 5
   غسيلCombined organic layers were washed with brine
6. 6
   تجفيفdried over anhydrous MgSO4
7. 7
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

A mixture of 5-bromofuran-2-carboxylic acid (2.64 g, 13.8 mmol), (cyclohexylmethyl)bromide (2.62 g, 14.8 mmol), K2CO3 (2.30 g, 16.64 mmol) in anhydrous NMP was stirred under Ar at +70° C. for 8 hrs after which additional (cyclohexylmethyl)bromide (1.55 g, 8.75 mmol) was added. Stirring continued overnight then the reaction mixture was concentrated under reduced pressure. The residue was partitioned between aqueous NaHCO3 (10%) and hexanes, and then aqueous layer was extracted with hexanes. Combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to give cyclohexylmethyl 5-bromofuran-2-carboxylate as a light yellow oil. Yield (2.22 g, 56%); 1H NMR (400 MHz, CDCl3) δ 7.10 (d, J=3.9 Hz, 1H), 6.44 (d, J=3.4 Hz, 1H), 4.10 (d, J=6.4 Hz, 2H), 1.64-1.84 (m, 6H), 1.12-1.34 (m, 3H), 0.95-1.09 (m, 2H).

المصدر