Water → [5-tert-Butyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazol-3-yl]-methanol

HRID 508614ノート

反応式

HRID 508614 の反応式
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:8]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[N:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.O>C1COCC1>[C:11]([C:9]1[N:8]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][CH:16]=2)[N:7]=[C:6]([CH2:4][OH:3])[CH:10]=1)([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 596493465-tert-Butyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester

生成物 1

HCID 67992518[5-tert-Butyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazol-3-yl]-methanol収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of compound 3h (0.8 g, 2.28 mmol) in 25 mL of THF was added LiAlH4 (0.14 g, 3.65 mmol). The reaction mixture was stirred for 6 hours at room temperature. EtOAc (50 mL) and water (50 mL) were added successively. The solvent was removed in vacuo and the resulting solid was filtered. The crude product was purified by column chromatography (EtOAc/Hexanes=7/3) to give the titled compound (0.56 g, 80% yield) as a white solid. mp 143.0-146.5° C. 1H NMR (300 MHz, DMSO-d6): δ 8.06 (d, J=8 Hz, 2H), 7.68 (d, J=8 Hz, 2H), 6.26 (s, 1H), 5.10 (t, J=6 Hz, 1H), 4.39 (d, J=6 Hz, 2H), 3.32 (s, 3H), 1.14 (s, 9H).

後処理

  1. customThe solvent was removed in vacuo
  2. filtrationthe resulting solid was filtered
  3. customThe crude product was purified by column chromatography (EtOAc/Hexanes=7/3)

出典と根拠

ORDレコード
ord-353e906e78b3443abb071195ef27aa62
出典データセット
uspto-grants-2015_08
特許番号
US09096532B2

反応ノート

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