Methanol → 1-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1h-pyrazole-4-carboxylic acid

HRID 1505287ノート

反応式

HRID 1505287 の反応式
C[O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[CH:9]=1)=[O:4].[OH-].[Na+].CO>C1COCC1.O>[Cl:25][C:23]1[CH:24]=[C:19]([C:13]2([C:15]([F:18])([F:16])[F:17])[O:12][N:11]=[C:10]([N:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[N:7]3)[CH2:14]2)[CH:20]=[C:21]([Cl:26])[CH:22]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 584979541-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1H-pyrazole-4-carboxylic acid methyl ester

生成物 1

HCID 584979271-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1h-pyrazole-4-carboxylic acid収率 91.2%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a solution of methyl ester of example 19.1 (513 mg) in 12.5 ml THF:water (4:1) was added sodium hydroxide (75 mg). The reaction mixture was stirred at room temperature for 3 hours before adding 2 ml of methanol. The reaction was stirred overnight before evaporation of the solvent in vacuo. The aqueous layer was extracted with ethyl acetate before being acidified. It was then extracted several times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford the title acid (452 mg) as a yellow solid. 1H-NMR (CDCl3, 400 MHz): 8.55 (s, 1H), 8.05 (s, 1H), 7.50 (m, 2H), 7.45 (m, 1H), 4.35 (d, 1H), 4.00 (d, 1H).

後処理

  1. stirringThe reaction was stirred overnight before evaporation of the solvent in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionIt was then extracted several times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-67a4a8d983254ad081fcbd0c746e136c
出典データセット
uspto-grants-2015_12
特許番号
US09216973B2

反応ノート

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