تفاعل #1481745

معادلة التفاعل

ethyl 2-hydroxyisobutyrate

2,5-bis(methyl sulfonyl) pyridine

sodium hydride

→

2-ethoxy-5-methylsulfonylpyridine

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to room temperature
2. 2
   أخرىwas partitioned between saturated aqueous ammonium chloride (200 mL) and ether (200 mL)
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwas washed with water and brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated to dryness
8. 8
   أخرىthe residue was purified by flash column chromatography on silica gel eluting with 0 to 80% ethyl acetate in hexane

الإجراء التجريبي

A mixture of ethyl 2-hydroxyisobutyrate (0.41 mL, 3.0 mmol), 2,5-bis(methyl sulfonyl) pyridine (J. Heterocycl. Chem. 1985, 22, 1583) (0.70 g, 3.0 mmol) and sodium hydride (60% dispersion in mineral oil, 0.14 g, 3.6 mmol) in 30 mL of anhydrous DMF was heated at 80° C. overnight. The reaction mixture was cooled to room temperature, and was partitioned between saturated aqueous ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated and was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness, and the residue was purified by flash column chromatography on silica gel eluting with 0 to 80% ethyl acetate in hexane to give the title compound as a 1:1 mixture with 2-ethoxy-5-methylsulfonylpyridine. LC-MS: m/e 288 (M+H)+ (0.70 min).

المصدر