Propylene Oxide → 1-(5-(Hydroxymethyl)-3-nitro-1H-pyrazol-1-yl)propan-2-ol

HRID 592992ノート

反応式

HRID 592992 の反応式
[N+:1]([C:4]1[CH:8]=[C:7]([CH2:9][OH:10])[NH:6][N:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][CH:18]1[CH2:20][O:19]1>ClCCl>[OH:10][CH2:9][C:7]1[N:6]([CH2:17][CH:18]([OH:19])[CH3:20])[N:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=1

参加物

5

反応物 3

HCID 6378Propylene OxideHCID 10796Cesium carbonateHCID 178526711HCID 178526711、化合物

生成物 1

HCID 866844761-(5-(Hydroxymethyl)-3-nitro-1H-pyrazol-1-yl)propan-2-ol収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
30 °C

実験手順

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with (3-nitro-1H-pyrazol-5-yl)methanol (0.57 g, 4.0 mmol), Cs2CO3 (261 mg, 0.8 mmol), and 2-methyloxirane (20 mL). The mixture was stirred at 30° C. for 2 days. The mixture was cooled to room temperature and diluted with dichloromethane (100 mL). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 250a (0.40 g, 50%) as a white solid. MS-ESI: [M+H]+ 202.3

後処理

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with 30:1 dichloromethane/methanol

出典と根拠

ORDレコード
ord-d4c93b4b27b842bba6fa2bd928ac756b
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

反応ノート

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