Water → HCID 21105731、化合物

HRID 1354479ノート

反応式

HRID 1354479 の反応式
Cl[C:2](=[N:13][OH:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])#[CH:16].C(N(CC)CC)C.O>O1CCCC1>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([C:2]2[CH:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[CH:20]=[O:21])[O:14][N:13]=2)=[CH:4][CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 27716443-EthynylbenzaldehydeHCID 73013045HCID 73013045、化合物

生成物 1

HCID 21105731HCID 21105731、化合物収率 54.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution (20 ml) of 1-[chloro(hydroxyimino)methyl]-4-trifluoromethylbenzene (0.849 g) and 3-ethynylbenzaldehyde (0.521 g) in tetrahydrofuran was added dropwise a solution (10 ml) of triethylamine (1.12 ml) in tetrahydrofuran at 0° C. This mixture was stirred overnight at room temperature and poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1, volume ratio) and recrystallized from hexane-ethyl acetate to give 3-[3-(4-trifluoromethylphenyl)-5-isoxazolyl]benzaldehyde (0.660 g, yield 52%) as colorless needle crystals. melting point: 151–152° C.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1, volume ratio)
  6. customrecrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-e662725d578e45e1a822aa67694b188d
出典データセット
uspto-grants-2007_05
特許番号
US07223791B2

反応ノート

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