Sodium Bicarbonate → HCID 68219039、化合物

HRID 241447

反応式

HRID 241447 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=1.[CH2:13]([Mg]Br)[CH3:14].C([O-])(O)=O.[Na+]>C1COCC1>[F:12][C:2]([F:11])([F:1])[C:3]1[N:8]=[CH:7][C:6]([CH:9]([OH:10])[CH2:13][CH3:14])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 178418443HCID 178418443、化合物

生成物 1

HCID 68219039HCID 68219039、化合物収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Dissolve 6-trifluoromethyl-pyridine-3-carboxaldehyde (3.526 g, 20.136 mmol) in THF (50 mL). Add ethylmagnesium bromide (3.0 M in Et2O, 7.38 mL, 22.1 mmol) quickly. Stir 30 minutes. Pour the reaction mixture into a saturated NaHCO3 aqueous solution (100 mL). Extract with EtOAc (3×50 mL). Wash the combined organic extracts with a saturated NaCl aqueous solution (75 mL). Dry the organic extracts over Na2SO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the residue by flash chromatography (Analogix® 40 g @ 40 mL/min) eluting with a gradient of EtOAc/hexanes (5% to 50%) over 30 minutes to give the title compound (2.01 g, 49% yield) as a yellow oil. 1H NMR (400.43 MHz, d6-DMSO) δ 8.66 (d, J=1.6 Hz, 1H), 7.95 (dd, J=1.9, 8.1 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 5.47 (d, J=4.5 Hz, 1H), 4.60 (q, J=5.8 Hz, 1H), 1.65-1.59 (m, 2H), 0.79 (t, J=7.4 Hz, 3H).

後処理

  1. extractionExtract with EtOAc (3×50 mL)
  2. washWash the combined organic extracts with a saturated NaCl aqueous solution (75 mL)
  3. dry with materialDry the organic extracts over Na2SO4
  4. filtrationfilter
  5. customcollect the filtrate
  6. concentrationand concentrate the filtrate under reduced pressure
  7. customPurify the residue by flash chromatography (Analogix® 40 g @ 40 mL/min)
  8. washeluting with a gradient of EtOAc/hexanes (5% to 50%) over 30 minutes

出典と根拠

ORDレコード
ord-8c8fa22a41c5438c97d12ef1faa9ee45
出典データセット
uspto-grants-2014_02
特許番号
US08648200B2

関連ノート

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