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

HRID 433017노트

반응식

HRID 433017 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e433f6f7a72945a8848cfff19cef3189
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664395B2

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