Water → 2,2-Difluoro-2-(2-pyridyl)ethylazide

HRID 1795286ノート

反応式

HRID 1795286 の反応式
[F:1][C:2]([F:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:3]OS(C(F)(F)F)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C=O)C>[N:19]([CH2:3][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([F:18])[F:1])=[N+:20]=[N-:21]

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 110662242,2-Difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate

生成物 1

HCID 118054052,2-Difluoro-2-(2-pyridyl)ethylazide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 5.5 g of trifluoro-methanesulfonic acid 2,2-difluoro-2-pyridin-2-yl-ethyl ester 1–4 in 70 mL of DMF was added 6.74 g (104 mmol) of sodium azide under Ar. The mixture was heated to 60° C. overnight. A second batch was run in the same manner, and after cooling to rt, both reactions were poured into 600 mL of water, and extracted with 3×500 mL of ether. The combined extracts were washed with brine, dried over Na2SO4 and concentrated at reduced pressure to give an oil that was purified by SiO2 (10×6 cm) using hexane 1:3 EtOAc-hexane and 1:1 EtOAc-hexane. The product-containing fractions were concentrated at reduced pressure to give the product as a yellow oil: 1H NMR (CDCl3) δ 4.05 (t, 2H), 7.4–7.45 (m, 1H), 7.73 (d, 1H), 7.83–7.89 (m, 1H), 8.67 (d, 1H).

後処理

  1. temperatureafter cooling to rt
  2. extractionextracted with 3×500 mL of ether
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated at reduced pressure
  6. customto give an oil that
  7. customwas purified by SiO2 (10×6 cm)
  8. concentrationThe product-containing fractions were concentrated at reduced pressure

出典と根拠

ORDレコード
ord-0b7de5de85474462948e6eb31a1e10b3
出典データセット
uspto-grants-2006_04
特許番号
US07026324B2

反応ノート

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