Water → 2-nitro-7-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]oxazine

HRID 451492ノート

反応式

HRID 451492 の反応式
Br[C:2]1[N:6]([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:9][O:10][Si](C(C)(C)C)(C)C)[N:5]=[C:4]([N+:24]([O-:26])=[O:25])[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[N+:24]([C:4]1[N:3]=[C:2]2[O:10][CH2:9][CH2:8][CH:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:6]2[N:5]=1)([O-:26])=[O:25]

参加物

5

反応物 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 673344335-Bromo-1-(3-(tert-butyldimethylsilyloxy)-1-phenylpropyl)-3-nitro-1H-1,2,4-triazole

生成物 1

HCID 673366942-nitro-7-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[5,1-b][1,3]oxazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 5-bromo-1-(3-(tert-butyldimethylsilyloxy)-1-phenylpropyl)-3-nitro-1H-1,2,4-triazole (510 mg, 1.16 mmol) in tetrahydrofurane (11.6 mL) was added under an atmosphere of nitrogen at room temperature 1 M tetrabutyl ammonium fluoride solution in tetrahydrofurane (3.47 mL, 3.47 mmol). The yellow solution was stirred at room temperature over night. Water was added and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a light yellow solid (174 mg, 61%) after column chromatography on silica gel using a gradient from heptane/ethyl acetate 4:1 to 1:1 (v/v) as eluent. MS ISP (m/e): 247.2 (100) [(M+H)+], 264.1 (36). 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.42-7.38 (m, 3H), 7.09 (d, 2H), 5.61 (t, 1H), 4.56 (m, 2H), 2.77 (m, 1H), 2.42 (m, 1H).

後処理

  1. extractionthe aqueous phase was extracted twice with ethyl acetate
  2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-6fe9f8502ffc4679bef91278a651db02
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

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