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

HRID 2261741ノート

反応式

HRID 2261741 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-41b261c9f6d041d9add01532e368ddd8
出典データセット
uspto-grants-2010_12
特許番号
US07846960B2

反応ノート

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