Hydrochloric Acid → 6-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid

HRID 927527

반응식

HRID 927527 반응식
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.C[O:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14](Cl)[N:13]=1)=[O:11].Cl>O>[CH:3]1([CH2:6][O:7][C:14]2[N:13]=[C:12]([C:10]([OH:11])=[O:9])[CH:17]=[CH:16][C:15]=2[C:18]([F:21])([F:19])[F:20])[CH2:5][CH2:4]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 70701015Methyl 6-chloro-5-(trifluoromethyl)picolinate

생성물 1

HCID 710874576-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid수율 85%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Sodium hydride (1.1 g, 31.4 mmol) was added in portions to cyclopropylmethanol (20 mL) and the mixture was stirred at room temperature for 0.5 hours. 6-Chloro-5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (1.5 g, 6.3 mmol) was added and the resulting solution was stirred at 80° C. for 1 h. Water (20 mL) was added; the solution was acidified with 6 N hydrochloric acid and then concentrated to give a residue which was partitioned between water (30 mL) and ethyl acetate (20 mL). The aqueous solution was extracted with ethyl acetate (2×20 mL) and the combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude target compound. The crude target compound was purified by column chromatography (silica gel, 10 g, 15% ethyl acetate in petroleum ether) to give the title compound (1.4 g, 85%) as white solid; MS (EI): m/e=262.0 [M+H]+.

후처리

  1. stirringthe resulting solution was stirred at 80° C. for 1 h
  2. concentrationconcentrated
  3. customto give a residue which
  4. customwas partitioned between water (30 mL) and ethyl acetate (20 mL)
  5. extractionThe aqueous solution was extracted with ethyl acetate (2×20 mL)
  6. washthe combined organic phase was washed with brine (20 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude target compound
  11. customThe crude target compound was purified by column chromatography (silica gel, 10 g, 15% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-4ffc865813e3477cb999f58322417e10
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290451B2

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