Tributylamine → HCID 86618521、化合物

HRID 2239887ノート

反応式

HRID 2239887 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.C(OC(=O)C)(=[O:17])C.C(N(CCCC)CCCC)CCC.[Cl-].[NH4+]>ClCCCl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:10])[O:11][C:12](=[O:17])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 7622TributylamineHCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 2758814ethyl 2-(3-chlorophenyl)-2-oxoacetate

生成物 1

HCID 86618521HCID 86618521、化合物

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 111,2-Dichloroethane溶媒

実験手順

To a flask was added ethyl 2-(3-chlorophenyl)-2-oxoacetate (1.8 g, 8.47 mmol) and acetic anhydride (1.60 ml, 16.93 mmol) in DCE (5 ml) at RT. To the resulting solution was added titanium(IV) chloride (16.93 ml, 16.93 mmol) and tributylamine (2.42 ml, 10.16 mmol). The solution was heated to reflux for 12 hours. The solution was then cooled in ice, and a solution of ammonium chloride was added. The mixture was stirred for 30 min. LC/MS indicated all starting material was gone. The solution was washed with 1×NH4Cl, 1N HCl, water, dried and concentrated in vacuo to provide 3-(3-chlorophenyl)furan-2,5-dione which was used as is in the next reaction. LC/MS, m/e 209 (M+1). HPLC Rt, 2.89 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min. hold at 100% B 1 min, flow rate 4 mL/min.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux for 12 hours
  3. temperatureThe solution was then cooled in ice
  4. washThe solution was washed with 1×NH4Cl, 1N HCl, water
  5. customdried
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bcc4d356e4914ac38c1ce5bab8aa2622
出典データセット
uspto-grants-2010_05
特許番号
US07723336B2

反応ノート

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