Tributylamine → HCID 86618521, 화합물

HRID 2239887노트

반응식

HRID 2239887 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 86618521HCID 86618521, 화합물

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bcc4d356e4914ac38c1ce5bab8aa2622
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723336B2

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