Sodium Bicarbonate → 2,2-Dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-1-ol

HRID 2279836ノート

反応式

HRID 2279836 の反応式
[CH3:1][C:2]([CH3:26])([CH2:18][O:19]C1CCCCO1)[CH2:3][N:4]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[N:5]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+]>CCO>[CH3:1][C:2]([CH3:26])([CH2:3][N:4]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[N:5]1)[CH2:18][OH:19]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 866977761-[2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2 回

生成物 1

HCID 678124422,2-Dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-1-ol収率 57.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

1-[2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 47C, 539 mg, 1.48 mmol) was dissolved in EtOH (2.64 mL) and p-TsOH.H2O (56.3 mg, 0.296 mmol) was added to the reaction mixture. The reaction was left to stir at rt for 16 hrs. Solid NaHCO3 (1.24 g, 14.8 mmol) was added to the reaction mixture and left to stir at rt for an additional 30 min. The reaction mixture was quenched with water and then extracted with EtOAc. The organic layer was washed with sat. NaHCO3 (1×), brine (2×), extracted, dried over sodium sulfate, filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash® Rf system [0-30% Acetone/Heptanes] to afford 237 mg of the title compound (57%). MS (ESI): m/z=281.38 [M+H]+. UPLC: tR=1.12 min (UPLC-TOF: polar—2 min).

後処理

  1. waitThe reaction was left
  2. waitleft
  3. stirringto stir at rt for an additional 30 min
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with sat. NaHCO3 (1×), brine (2×)
  7. extractionextracted
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. custompurified

出典と根拠

ORDレコード
ord-c3ff203308734cb79352d93160d43f61
出典データセット
uspto-grants-2015_09
特許番号
US09133224B2

反応ノート

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