Diisobutylaluminum hydride → (1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

HRID 2261741노트

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HRID 2261741 반응식
C[O:2][C:3]([C:5]1[N:6]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[N:7]=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=O.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:20])[C:13]=1[N:6]1[C:5]([CH2:3][OH:2])=[C:9]([CH:10]([CH3:12])[CH3:11])[CH:8]=[N:7]1

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 574432552-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazole-3-carboxylic acid methyl ester

생성물 1

HCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol수율 82.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 0° C. solution of 2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazole-3-carboxylic acid methyl ester (2.2 g, 6.8 mmol) in THF (30 mL) is added DIBAL-H (33.7 mL, 1M in toluene). The reaction mixture is stirred at ambient temperature overnight. The reaction is quenched by the addition of methanol and is concentrated under reduced pressure. The residue is partitioned between 5N NaOH and EtOAc. The layers are separated and the organic layer is filtered through a pad of diatomaceous earth. The filtrate is concentrated under reduced pressure to give the title compound as a light yellow solid, (1.6 g, 80%). 1H NMR (400 MHz, CDCl3): δ 7.67 (s, 1H), 7.44 (d, 2H), 7.34 (dd, 1H), 4.45 (s, 2H), 3.00 (m, 1H), 1.32 (d, 6H).

후처리

  1. customThe reaction is quenched by the addition of methanol
  2. concentrationis concentrated under reduced pressure
  3. customThe residue is partitioned between 5N NaOH and EtOAc
  4. customThe layers are separated
  5. filtrationthe organic layer is filtered through a pad of diatomaceous earth
  6. concentrationThe filtrate is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-41b261c9f6d041d9add01532e368ddd8
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846960B2

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