Potassium Carbonate → 3-(2-Chloro-4-fluorophenoxy)-1-(diphenylmethyl)azetidine

HRID 225827

反応式

HRID 225827 の反応式
CS([O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[Cl:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1O>C(#N)C>[Cl:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 748142-Chloro-4-fluorophenolHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

生成物 1

HCID 150422263-(2-Chloro-4-fluorophenoxy)-1-(diphenylmethyl)azetidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 1-(diphenylmethyl)-3-azetidinyl methanesulfonate (363.8 g, 1.15 mol), potassium carbonate (330 g, 2.38 mol) and 2-chloro-4-fluorophenol (140 g, 0.96 mol) in acetonitrile (2.5 L) was heated under reflux for 4.5 hours. The cooled reaction mixture was then concentrated in vacuo and the residue was partitioned between ethyl acetate (1 L) and water (500 mL). The organic layer was separated, dried over sodium sulfate concentrated in vacuo and the residue was triturated with ethyl acetate/pentane/dichloromethane, 90:10:1, to afford the title compound as a white solid in quantitative yield, 350 g. 1H NMR(400 MHz, CDCl3) δ: 3.19(m, 2H), 3.75(m, 2H), 4.45(m, 1H), 4.78(m, 1H), 6.60(m, 1H), 6.83(m, 1H), 7.14(m, 1H), 7.18-7.50(m, 10H)

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 4.5 hours
  3. customThe cooled reaction mixture
  4. concentrationwas then concentrated in vacuo
  5. customthe residue was partitioned between ethyl acetate (1 L) and water (500 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customthe residue was triturated with ethyl acetate/pentane/dichloromethane, 90:10:1

出典と根拠

ORDレコード
ord-17060589234849aba36ee41a94192852
出典データセット
uspto-grants-2009_07
特許番号
US07557131B2

関連ノート

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