Diisobutylaluminum hydride → 1-Isopropyl-1H-benzo[D][1,2,3]triazole-6-carbaldehyde

HRID 433017ノート

反応式

HRID 433017 の反応式
CON(C)[C:4]([C:6]1[CH:17]=[CH:16][C:9]2[N:10]=[N:11][N:12]([CH:13]([CH3:15])[CH3:14])[C:8]=2[CH:7]=1)=[O:5].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH:13]([N:12]1[C:8]2[CH:7]=[C:6]([CH:4]=[O:5])[CH:17]=[CH:16][C:9]=2[N:10]=[N:11]1)([CH3:15])[CH3:14]

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 57350071N-Methoxy-N-methyl-1-(propan-2-yl)-1H-benzotriazole-6-carboxamide

生成物 1

HCID 116153161-Isopropyl-1H-benzo[D][1,2,3]triazole-6-carbaldehyde収率 69%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-78 °C

実験手順

To a stirred, cold (−78° C.) solution of 3-isopropyl-3H-benzotriazole-5-carboxylic acid methoxy-methyl-amide (4.26 g) in 20 mL of toluene was added drop-wise 17.2 mL of DIBAL in toluene (1 M). The mixture was stirred for 1 hour at −78° C. before warming to 0° C. The reaction was quenched with aqueous 1 N hydrochloric acid, diluted with water and extracted with ethyl acetate (3 times). The combined extracts were washed with water, brine, dried (sodium sulfate), filtered, and the filtrate was concentrated to give a yellow oil. This oil was purified by flash chromatography (eluting with 2:1 hexanes/ethyl acetate) to give 2.24 g of 3-isopropyl-3H-benzotriazole-5-carbaldehyde as a yellow oil which crystallized upon standing; MS 190 M+1.

後処理

  1. temperaturebefore warming to 0° C
  2. customThe reaction was quenched with aqueous 1 N hydrochloric acid
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate (3 times)
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customto give a yellow oil
  10. customThis oil was purified by flash chromatography (eluting with 2:1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-e433f6f7a72945a8848cfff19cef3189
出典データセット
uspto-grants-2003_12
特許番号
US06664395B2

反応ノート

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