Potassium peroxymonosulphate → 5-Chloro-6-cyclopropylpyridin-3-OL

HRID 512063ノート

反応式

HRID 512063 の反応式
[Cl:1][C:2]1[C:3]([CH:17]2[CH2:19][CH2:18]2)=[N:4][CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.S([O-])(O[O-])(=O)=[O:21].[K+].[K+]>CC(C)=O.O.CC(OC)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([OH:21])[CH:5]=[N:4][C:3]=1[CH:17]1[CH2:19][CH2:18]1

参加物

6

反応物 2

HCID 10313463Potassium peroxymonosulphateHCID 58042381(5-Chloro-6-cyclopropylpyridin-3-yl)boronic acid pinacol ester

生成物 1

HCID 580424875-Chloro-6-cyclopropylpyridin-3-OL収率 42%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
0 °C

実験手順

3-Chloro-2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 41, 3.092 mmol assuming 100% in previous step) was dissolved in acetone (10.0 mL) and cooled to 0° C. with an ice bath. Then potassium peroxymonosulfate (2.55 g, 4.15 mmol) in water (10.0 mL) was added dropwise to the mixture and stirred at this temperature for 1 hour. The reaction was then diluted in TBME (25.0 mL) and washed with brine (3×25.0 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified with silica gel chromatography eluting with 0 to 30% EtOAc in heptane to yield the title compound as a pale yellow solid (0.220 g, 1.28 mmol, 42% over 2 steps).

後処理

  1. washwashed with brine (3×25.0 mL)
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude product was purified with silica gel chromatography
  6. washeluting with 0 to 30% EtOAc in heptane

出典と根拠

ORDレコード
ord-a34fcdbbf675419da01a0c5b5b82f83c
出典データセット
uspto-grants-2015_08
特許番号
US09102621B2

反応ノート

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