Trifluoroacetic anhydride → 2-(2,4-Difluorophenyl)-5-methyl-2H-1,2,3-triazole-4-methanol

HRID 623709노트

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HRID 623709 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]([CH3:14])[C:11]([CH3:15])=[N+:10]1[O-].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:20]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]([CH2:14][OH:20])[C:11]([CH3:15])=[N:10]1

참가 물질

5

반응물 2

HCID 9845Trifluoroacetic anhydrideHCID 901098102-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide2회

생성물 1

HCID 901092522-(2,4-Difluorophenyl)-5-methyl-2H-1,2,3-triazole-4-methanol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To a solution of 2-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide (i.e. the product of Step A, 1.78 g, 7.0 mmol) in tetrahydrofuran (14 mL) was added trifluoroacetic anhydride (2.5 mL, 17.5 mmol). The reaction mixture was stirred at 110° C. in the microwave for 75 min. The mixture was diluted with ethyl acetate, washed successively with 1.0 M aqueous sodium hydroxide and 50% aqueous sodium hydroxide, dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to obtain the title compound (0.59 g) as a colorless solid.

후처리

  1. washwashed successively with 1.0 M aqueous sodium hydroxide and 50% aqueous sodium hydroxide
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customThe crude material was purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-9ac76b9069f9454cbc7121c5c424d5ac
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302999B2

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