Lithium hydroxide, monohydrate → HCID 58374151、化合物

HRID 1506284ノート

反応式

HRID 1506284 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 58374151HCID 58374151、化合物収率 96.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8a1105377b0348e6b8efec4720026e5a
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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