تفاعل #309762

معادلة التفاعل

sodium carbonate

hydrogen fluoride

polyethylene

1-oxa-spiro[2.4]heptane-2-carbonitrile

→

desired compound

المردود 58.1%

(1-Fluoro-cyclopentyl)-hydroxy-acetonitrile

المردود 58.1%

المذيبات

pyridine

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is cooled at 0° C.
2. 2
   استخلاصThe aqueous layer is extracted with diethyl ether
3. 3
   غسيلwashed with water and brine
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   أخرىthe solvent is removed
7. 7
   أخرىThe residue is purified by chromatography in a 20 g silica gel cartridge
8. 8
   غسيلeluting with hexane:diethyl ether (100:0 to 80:20)

الإجراء التجريبي

Anhydrous dichloromethane (3 mL) and a 70% w/w solution of hydrogen fluoride (2.68 mL, 20.44 mmol) in pyridine are mixed in a polyethylene bottle at 0° C. under a nitrogen atmosphere. A solution of 1-oxa-spiro[2.4]heptane-2-carbonitrile (3.30 g, 26.76 mmol) in anhydrous dichloromethane (3.2 mL) is added slowly. The reaction is stirred at 0° C. for 1 h and at room temperature for 1 h. The mixture is cooled at 0° C. and a saturated solution of sodium carbonate is added carefully. The aqueous layer is extracted with diethyl ether. The organic layers are combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the solvent is removed. The residue is purified by chromatography in a 20 g silica gel cartridge eluting with hexane:diethyl ether (100:0 to 80:20) to obtain 1.7 g of desired compound as a colourless oil. 1H NMR (CDCl3) δ (ppm): 4.47 (d, 1H), 3.50 (bs, 1H), 2.12-1.67 (m, 8H).

المصدر