Sodium Carbonate → (1-Fluorocyclopentyl)(hydroxy)acetonitrile

HRID 222580

反応式

HRID 222580 の反応式
[FH:1].[O:2]1[C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:3]1[C:9]#[N:10].C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1.ClCCl>[F:1][C:4]1([CH:3]([OH:2])[C:9]#[N:10])[CH2:8][CH2:7][CH2:6][CH2:5]1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 14917Hydrofluoric AcidHCID 5489741-Oxaspiro(2.4)heptane-2-carbonitrileHCID 178435160HCID 178435160、化合物

生成物 1

HCID 12728544(1-Fluorocyclopentyl)(hydroxy)acetonitrile収率 58.1%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  1. temperatureThe mixture is cooled at 0° C.
  2. extractionThe aqueous layer is extracted with diethyl ether
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed
  7. customThe residue is purified by chromatography in a 20 g silica gel cartridge
  8. washeluting with hexane:diethyl ether (100:0 to 80:20)

出典と根拠

ORDレコード
ord-4a95bf4964c24cd6be35cb541c2a2421
出典データセット
uspto-grants-2012_06
特許番号
US08207344B2

関連ノート

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