Potassium Carbonate → 1-Phenyl-5-(5-trifluoromethyl-thiophen-3-yloxy)-1H-tetrazole

HRID 6973

반응식

HRID 6973 반응식
[F:1][C:2]([F:10])([F:9])[C:3]1[S:7][CH:6]=[C:5]([OH:8])[CH:4]=1.Cl[C:12]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]=[N:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:17]1([N:16]2[C:12]([O:8][C:5]3[CH:4]=[C:3]([C:2]([F:10])([F:9])[F:1])[S:7][CH:6]=3)=[N:13][N:14]=[N:15]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 110842734-Hydroxy-2-(trifluoromethyl)thiophene

생성물 1

HCID 220194661-Phenyl-5-(5-trifluoromethyl-thiophen-3-yloxy)-1H-tetrazole수율 68%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of 5-trifluoromethyl-thiophen-3-ol (2.0 g, 11.9 mmol) in dry acetone (480 mL) containing 5-chloro-1-phenyl-1H-tetrazole (2.1 g, 11.9 mmol) and K2CO3 (3.3 g, 23.8 mmol) is maintained at reflux with careful exclusion of moisture overnight. The acetone is removed under reduced pressure and the residue is partitioned between CH2Cl2 (500 mL) and H2O (50 mL). The organic extracts are washed with brine, then dried (Na2SO4), filtered and concentrated. The crude product is chromatographed on silica gel, eluting with EtOAc:Hex (1:80) to afford the title compound (2.5 g, 68%) as a white solid.

후처리

  1. temperatureis maintained
  2. temperatureat reflux with careful exclusion of moisture overnight
  3. customThe acetone is removed under reduced pressure
  4. customthe residue is partitioned between CH2Cl2 (500 mL) and H2O (50 mL)
  5. washThe organic extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is chromatographed on silica gel
  10. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-97bd380cae1c4e708eb824535de2f9eb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084170B2

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