Diisobutylaluminum hydride → [3-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-yl]methanol

HRID 424811ノート

反応式

HRID 424811 の反応式
C([O:3][C:4]([C:6]1[N:7]([C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[N:8]=[N:9][C:10]=1[C:11]([F:14])([F:13])[F:12])=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=1[N:7]1[C:6]([CH2:4][OH:3])=[C:10]([C:11]([F:13])([F:14])[F:12])[N:9]=[N:8]1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 667041363-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazole-4-carboxylic Acid Ethyl Ester

生成物 1

HCID 66704107[3-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-yl]methanol収率 97.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 3-(2,6-dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (28 g, 79 mmol) in THF (200 mL) is added dropwise 1M DIBAL (166 mL, 166 mmol) keeping the temperature below 5° C. After the addition, the bath is removed and the reaction is stirred for 18 h. The reaction is cooled to 0° C. and ether (300 mL) is added. The reaction is quenched with 1N HCl (250 mL) dropwise keeping the temperature below 15° C. The layers are separated and the water layer is washed with Ether (100 mL). The organics are combined and washed with water, brine, and dried with Na2SO4. The organic layer is concentrated to dryness to yield the title compound (24 g, 97%) and is used with no further purification. ES/MS m/e 312.0 (M+1).

後処理

  1. customthe temperature below 5° C
  2. additionAfter the addition
  3. customthe bath is removed
  4. additionether (300 mL) is added
  5. customThe reaction is quenched with 1N HCl (250 mL)
  6. customthe temperature below 15° C
  7. customThe layers are separated
  8. washthe water layer is washed with Ether (100 mL)
  9. washwashed with water, brine
  10. dry with materialdried with Na2SO4
  11. concentrationThe organic layer is concentrated to dryness

出典と根拠

ORDレコード
ord-facd9dea1d8c4a30ba9985adbcb35e4a
出典データセット
uspto-grants-2012_01
特許番号
US08106077B2

反応ノート

読み込み中…