Triethylamine → (E)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-one

HRID 1527967노트

반응식

HRID 1527967 반응식
[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][N:13]=[N:12][CH:11]=1)[CH2:3]P(=O)(OC)OC.C(N(CC)CC)C.[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C1COCC1>[Br:23][C:24]1[CH:31]=[CH:30][C:27](/[CH:28]=[CH:3]/[C:2]([C:10]2[CH:15]=[CH:14][N:13]=[N:12][CH:11]=2)=[O:1])=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 707414-BromobenzaldehydeHCID 86684793Dimethyl 2-oxo-2-(pyridazin-4-yl)ethylphosphonate

생성물 1

HCID 86684794(E)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-one수율 7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of dimethyl 2-oxo-2-(pyridazin-4-yl)ethylphosphonate (1.83 g, 7.95 mmol) in THF (18 mL) was added triethylamine (885 mg, 8.75 mmol) and 4-bromobenzaldehyde (1.49 g, 7.95 mmol) at 0° C. After 6 h the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. The residue was suspended in ethyl acetate and the title compound (824 mg, 36%) collected by filtration. Chromatography of the mother liquor (SiO2; ethyl acetate) produced a second crop of product (160 mg, 7%). Light yellow solid, MS: 288.9 [M+H]+.

후처리

  1. customAfter 6 h the reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. filtrationthe title compound (824 mg, 36%) collected by filtration

출처 및 근거

ORD 기록
ord-8f3ea2a39a7649aeb9e4cfa8bb7e7fe7
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090565B2

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