Lithium hydroxide, monohydrate → HCID 58374151, 화합물

HRID 1506284노트

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HRID 1506284 반응식
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14]CC)=[O:13])[C:8]=2[C:17]([F:20])([F:19])[F:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>CO.O>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[C:8]=2[C:17]([F:19])([F:20])[F:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 66955079Ethyl 5-phenyl-4-(trifluoromethyl)isoxazole-3-carboxylate

생성물 1

HCID 58374151HCID 58374151, 화합물수율 96.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of ethyl 5-phenyl-4-(trifluoromethyl)isoxazole-3-carboxylate (Intermediate I-5C, 3.6 g, 12.6 mmol) in methanol (100 mL) and water (20 mL) at room temperature was added lithium hydroxide, monohydrate (0.583 g, 13.9 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The methanol was removed under reduced pressure, and the residue was diluted with water (˜100 mL). Ethyl ether (200 mL) was added, and the pH of the aqueous layer was adjusted to <1 with a 1N aqueous solution of hydrochloric acid. The mixture was transferred to a separatory funnel, and after agitation, the layers were separated. The organic layer was washed with brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated to afford 5-phenyl-4-(trifluoromethyl)isoxazole-3-carboxylic acid (3.12 g, 12.13 mmol, 96% yield) as a white, crystalline solid. The compound had an HPLC retention time=2.58 minutes (condition B); MS:(M+Na)=279.95; 1H NMR (400 MHz, CDCl3) δ ppm 7.53-7.64 (m, 3H), and 7.70 (d, J=7.5 Hz, 2H).

후처리

  1. customThe methanol was removed under reduced pressure
  2. additionthe residue was diluted with water (˜100 mL)
  3. additionEthyl ether (200 mL) was added
  4. customThe mixture was transferred to a separatory funnel
  5. customafter agitation, the layers were separated
  6. washThe organic layer was washed with brine (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8a1105377b0348e6b8efec4720026e5a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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