Potassium Iodide → 3-{4-[(2-Butyl-5-nitro-1-benzofuran-3-yl) carbonyl]phenoxy}propan-1-ol

HRID 43298

反応式

HRID 43298 の反応式
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:9]([C:13]1[O:14][C:15]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:16]=2[C:17]=1[C:18](=[O:26])[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH2:10][CH2:11][CH3:12].Cl[CH2:35][CH2:36][CH2:37][OH:38]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:9]([C:13]1[O:14][C:15]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:16]=2[C:17]=1[C:18]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:35][CH2:36][CH2:37][OH:38])=[CH:23][CH:24]=1)=[O:26])[CH2:10][CH2:11][CH3:12]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 11473234(2-Butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone

生成物 1

HCID 566497733-{4-[(2-Butyl-5-nitro-1-benzofuran-3-yl) carbonyl]phenoxy}propan-1-ol収率 69.5%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
45 °C

実験手順

312 g (2.26 moles) of potassium carbonate, 11 g (0.066 moles) of potassium iodide and 11 g (0.034 moles) of tetrabutylammonium bromide are added to a solution of 222 g (0.655 moles) of 2-butyl-3-(4-hydroxybenzoyl)-5-nitro-benzofuran (formula (V)) in 1780 ml of DMF. The reaction mixture is heated to 50° C. and after approximately 30 minutes 100 g of 3-chloro-1-propanol are added dropwise. At the end of the dropwise addition, the reaction mixture is brought to 80-85° C. and left under stirring for 4-5 hours. Once the reaction is complete, the mixture is cooled to 40-50° C. and the inorganic salts are removed by filtering. The organic solvent is distilled at reduced pressure, maintaining the temperature around 60-70° C., and the residue is dissolved in 2220 ml of toluene. After performing three washing operations on the organic phase, each with 1130 ml of deionised water, the toluene is concentrated to residue. The crude product is dissolved with approximately 100 ml of ethyl acetate and the mixture is left under cooling at 0-4° C. for approximately 12 hours. The solid is filtered, the wet product is washed with a little ethyl acetate pre-cooled to 0-5° C. and it is dried under a vacuum at 40° C. for 6-7 hours. 181 g of 3-{4-[(2-butyl-5-nitro-1-benzofuran-3-yl)carbonyl]phenoxyl}propan-1-ol (formula (II)) are obtained.

後処理

  1. additionare added dropwise
  2. additionAt the end of the dropwise addition
  3. customis brought to 80-85° C.
  4. waitleft
  5. customthe inorganic salts are removed
  6. filtrationby filtering
  7. distillationThe organic solvent is distilled at reduced pressure
  8. temperaturemaintaining the temperature around 60-70° C.
  9. dissolutionthe residue is dissolved in 2220 ml of toluene
  10. concentrationeach with 1130 ml of deionised water, the toluene is concentrated to residue
  11. dissolutionThe crude product is dissolved with approximately 100 ml of ethyl acetate
  12. waitthe mixture is left
  13. temperatureunder cooling at 0-4° C. for approximately 12 hours
  14. filtrationThe solid is filtered
  15. washthe wet product is washed with a little ethyl acetate
  16. temperaturepre-cooled to 0-5° C.
  17. customit is dried under a vacuum at 40° C. for 6-7 hours

出典と根拠

ORDレコード
ord-b5acc2e7676d4d728fe2b8cf6ba6153e
出典データセット
uspto-grants-2013_09
特許番号
US08536350B2

関連ノート

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