Sodium Hydroxide → HCID 136078238、化合物

HRID 2378063ノート

反応式

HRID 2378063 の反応式
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3([C:29]([O:31]C)=[O:30])[CH2:28][CH2:27]3)[O:17][N:16]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[OH-].[Na+]>O1CCCC1.O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]3)[O:17][N:16]=2)=[CH:13][CH:14]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 68957642HCID 68957642、化合物2 回

生成物 1

HCID 136078238HCID 136078238、化合物収率 78.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution consisting of 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarboxylic acid methyl ester (Example 1, Compound D, 10 g) in tetrahydrofuran (100 mL) is added a 50 wt % sodium hydroxide in water solution (10 mL). The mixture is heated to 60° C. for 18 hours. The reaction mixture is concentrated under reduced pressure and partitioned between diethyl ether and water. The aqueous layer is washed with diethyl ether and acidified to pH 5 with concentrated aqueous hydrochloric acid. The aqueous phase is extracted with ethyl acetate. The combined extracts are washed with water and brine solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford the title compound (5.64 g); MS (APCI+) m/z 322 (MH+.)

後処理

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. custompartitioned between diethyl ether and water
  3. washThe aqueous layer is washed with diethyl ether
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. washThe combined extracts are washed with water and brine solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-18f1a7ab0a3e4143b71a10c6a1c8d655
出典データセット
uspto-grants-2008_12
特許番号
US07470715B2

反応ノート

読み込み中…