Water → HCID 21105731, 화합물

HRID 1354479노트

반응식

HRID 1354479 반응식
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

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 27716443-EthynylbenzaldehydeHCID 73013045HCID 73013045, 화합물

생성물 1

HCID 21105731HCID 21105731, 화합물수율 54.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e662725d578e45e1a822aa67694b188d
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223791B2

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