Water → 3-(3-Bromopropoxy-4-methoxyphenyl)phenylmethanone

HRID 235370ノート

反応式

HRID 235370 の反応式
O[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9]C=1)=O.[H-].[Na+].[Br:20][CH2:21][CH2:22][CH2:23]Br.[OH2:25].CN(C)[CH:28]=[O:29]>>[Br:20][CH2:21][CH2:22][CH2:23][O:25][C:3]1[CH:2]=[C:15]([O:16][CH3:17])[CH:14]=[CH:13][C:4]=1[C:5]1[CH:7]=[C:12]([CH:28]=[O:29])[CH:11]=[CH:10][CH:9]=1

参加物

6

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 41488933-Hydroxy-4-methoxybenzophenone

生成物 1

HCID 219600893-(3-Bromopropoxy-4-methoxyphenyl)phenylmethanone

反応条件

温度
90 °C

実験手順

A solution of 3-hydroxy-4-methoxybenzophenone (4.6 g, 20 mmol) in dimethylformamide (35 ml) was treated with sodium hydride (600 mg, 25 mmol) at 0° C. for 20 minutes, then 1,3-dibromopropane (5 g, 24.7 mmol) was added in one portion. The mixture was heated at 90° C. for 1 hour, and then stirred at room temperature for 2 hours. At the end of the reaction, the mixture was poured into water (500 ml) and extracted with ethyl acetate (400 ml). The ethyl acetate solution was washed with water, brine and dried over anhydrous MgSO4. The solvent was removed and the crude oil was purified by flash chromatography over a silica gel column (SIO2, 85 g; eluted with 3:1 hexane:dichloromethane, 1.6 l; 3:7 hexane: dichloromethane, 1.4 l). The pure product thus obtained weighed 4.67 g, (66%) as an oil. Recrystallization twice from isopropyl ether (500 ml) gave analytically pure 3-(3-bromopropoxy -4-methoxyphenyl)phenylmethanone (2.42 g), m.p.=81°-83° C.

後処理

  1. customAt the end of the reaction
  2. extractionextracted with ethyl acetate (400 ml)
  3. washThe ethyl acetate solution was washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed
  6. customthe crude oil was purified by flash chromatography over a silica gel column (SIO2, 85 g; eluted with 3:1 hexane:dichloromethane, 1.6 l; 3:7 hexane: dichloromethane, 1.4 l)
  7. customThe pure product thus obtained
  8. customRecrystallization twice from isopropyl ether (500 ml)

出典と根拠

ORDレコード
ord-5d9d5704916b4b5c9d5d90fbfebfa37a
出典データセット
uspto-grants-1997_01
特許番号
US05597842

反応ノート

読み込み中…