Sodium borohydride → 2-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-propan-1-ol

HRID 2261752노트

반응식

HRID 2261752 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:25])[CH:23]=[O:24])=[C:18]([CH3:26])[CH:17]=2)=[C:12]([CH:27]([CH3:29])[CH3:28])[CH:11]=[N:10]1.[BH4-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:25])[CH2:23][OH:24])=[C:18]([CH3:26])[CH:17]=2)=[C:12]([CH:27]([CH3:29])[CH3:28])[CH:11]=[N:10]1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 866354632-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-propionaldehyde

생성물 1

HCID 574432712-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-propan-1-ol수율 95%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a 0° C. solution of 2-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-propionaldehyde (753 mg, 1.74 mmol) in THF (17 mL) and MeOH (3 mL) is added sodium borohydride (198 mg, 5.23 mmol) portionwise. The reaction mixture is warmed to room temperature. After 2 h, the reaction is concentrated under reduced pressure and the residue is partitioned between Et2O (100 mL) and 1N HCl (30 mL). The aqueous layer is extracted with Et2O (100 mL) and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 30% EtOAc/Hex) to yield the title compound (715 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H), 7.43-7.40 (m, 2H), 7.33-7.28 (m, 1H), 7.04 (d, 1H, J=8.4 Hz), 6.64-6.58 (m, 2H), 4.79 (s, 2H), 3.68-3.63 (m, 2H), 3.14-3.16 (m, 1H), 2.99 (sept, 1H, J=7.0 Hz), 2.28 (s, 3H), 1.30 (d, 3H, J=7.0 Hz), 1.21 (d, 6H, J=7.0 Hz).

후처리

  1. concentrationthe reaction is concentrated under reduced pressure
  2. customthe residue is partitioned between Et2O (100 mL) and 1N HCl (30 mL)
  3. extractionThe aqueous layer is extracted with Et2O (100 mL)
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (0% to 30% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-a288c28e707e488188725f6954246034
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846960B2

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