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

HRID 508614노트

반응식

HRID 508614 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-353e906e78b3443abb071195ef27aa62
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096532B2

반응 노트

불러오는 중…