Sodium Bicarbonate → HCID 68219039, 화합물

HRID 241447

반응식

HRID 241447 반응식
[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

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 68219039HCID 68219039, 화합물수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8c8fa22a41c5438c97d12ef1faa9ee45
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648200B2

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