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

HRID 623709

反応式

HRID 623709 の反応式
[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

参加物

5

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 901098102-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ac76b9069f9454cbc7121c5c424d5ac
出典データセット
uspto-grants-2016_04
特許番号
US09302999B2

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