HCID 21477178、化合物 → HCID 54730488、化合物

HRID 2293683ノート

反応式

HRID 2293683 の反応式
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.Br[CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=1)[CH2:15][CH3:16].CC(C1C(=O)OC2C(C=1O)=CC=CC=2)(C)C1C=CC=CC=1>C(Cl)Cl>[Br:23][C:19]1[CH:18]=[C:17]([CH:14]([C:3]2[C:4](=[O:12])[O:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:15][CH3:16])[CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 21477178HCID 21477178、化合物HCID 546829304-HydroxycoumarinHCID 54724919HCID 54724919、化合物

生成物 1

HCID 54730488HCID 54730488、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
175 °C

実験手順

A mixture of 4-hydroxycoumarin (898 mg) and 1-bromo-1-(3-bromophenyl)propane of Preparation 39 (3.08 g) under nitrogen is sealed in a screw-cap vial and placed in an oil bath at 100° C. The mixture is heated to 175° C. over approximately 45 rain, and the resulting melt is stirred at this temperature for 45 rain, cooled to RT, diluted with methylene chloride (45 mL), washed with water (10 mL) and saline (10 mL), dried over sodium sulfate, and concentrated under reduced pressure to give a residue which is then chromatographed on silica gel (230-400 mesh, 350 g), eluting with a gradient of ethyl acetate/hexane (15/85-60/40). Pooling of fractions with an Rf =0.20 by TLC (ethyl acetate/hexane, 50/50) and removal of solvent gives the title compound.

後処理

  1. customis sealed in a screw-cap vial and
  2. customplaced in an oil bath at 100° C
  3. temperaturecooled to RT
  4. washwashed with water (10 mL) and saline (10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue which
  8. customis then chromatographed on silica gel (230-400 mesh, 350 g)
  9. washeluting with a gradient of ethyl acetate/hexane (15/85-60/40)
  10. customPooling of fractions with an Rf =0.20 by TLC (ethyl acetate/hexane, 50/50) and removal of solvent

出典と根拠

ORDレコード
ord-78796e94b9ac429db10b7d59d328d0e6
出典データセット
uspto-grants-1997_11
特許番号
US05686486

反応ノート

読み込み中…