Water → HCID 59556309、化合物

HRID 1172697

反応式

HRID 1172697 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:5][C:6]=1[CH:7]([OH:10])[CH2:8][CH3:9].CC(C)([O-])C.[K+].[F:27][C:28]1[CH:35]=[C:34](F)[C:33]([F:37])=[CH:32][C:29]=1[C:30]#[N:31].O>O1CCCC1.C(O)(C)(C)C>[F:27][C:28]1[CH:35]=[C:34]([O:10][CH:7]([C:6]2[S:5][C:4]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=3)=[N:3][C:2]=2[CH3:1])[CH2:8][CH3:9])[C:33]([F:37])=[CH:32][C:29]=1[C:30]#[N:31]

参加物

7

反応物 4

HCID 962WaterHCID 5938132,4,5-TrifluorobenzonitrileHCID 235491291-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-olHCID 23665647Potassium tert-butoxide

生成物 1

HCID 59556309HCID 59556309、化合物収率 95.5%

試薬・触媒・溶媒 2

HCID 6386tert-Butanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

To a solution of 900 mg of 1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol in 2 mL of tetrahydrofuran at 5° C. was slowly added 3.3 mL of a molar solution of potassium tert-butoxide in tert-butanol. After stirring at 5° C. for 30 minutes, the resulting solution was slowly added to a solution of 469 mg of 2,4,5-trifluoro-benzonitrile in 2 mL of tetrahydrofuran at −60° C. The resulting mixture was stirred for 1 h at −60° C. then stirred overnight allowing the temperature to warm up to room temperature. It was then poured into water and extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient from heptane 100 to heptane 80/ethyl acetate 20) to give 1.25 g of 2,5-difluoro-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-benzonitrile.

後処理

  1. customat 5° C.
  2. stirringThe resulting mixture was stirred for 1 h at −60° C.
  3. stirringthen stirred overnight
  4. temperatureto warm up to room temperature
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (gradient from heptane 100 to heptane 80/ethyl acetate 20)

出典と根拠

ORDレコード
ord-640d9a37120e4412a9ff258c71214264
出典データセット
uspto-grants-2010_11
特許番号
US07834030B2

関連ノート

読み込み中…