Triethylamine → 1-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethanol

HRID 273143노트

반응식

HRID 273143 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](Cl)=[N:6][OH:7].[CH3:12][CH:13]([OH:16])[C:14]#[CH:15].C(N(CC)CC)C>C1C=CC=CC=1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[CH:15]=[C:14]([CH:13]([OH:16])[CH3:12])[O:7][N:6]=2)[CH:9]=[CH:10][CH:11]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 724759113-Chloro-benzohydroximoyl chloride

생성물 1

HCID 670707661-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethanol

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 313Hydrochloric Acid용매

반응 조건

온도
0 °C

실험 절차

3-Chloro-benzohydroximoyl chloride (e.g. Kim, Jae Nyoung; Ryu, Eung K; J. Org. Chem. (1992), 57(24), 6649-50) (2.84 g, 14.8 mmol) was suspended in benzene (50 ml) and cooled to 0° C. 3-Butyn-2-ol (2.10 g, 29.9 mmol) and triethylamine (1.89 ml, 26.7 mmol) were added. The mixture was heated to 60° C. for 1.5 houes, cooled and diluted with benzene and 1N aqueous hydrochloric acid. After stirring, the separated benzene layer was evaporated to dryness and the crude purified via flash chromatography over silica using heptane/ethyl acetate=5/1 giving after drying in vacuo the title compound (0.49 g, 15%). 1H NMR (CDCl3), δ (ppm): 1.64 (d, 3 H), 5.07 (dq, 1 H), 6.50 (s, 1 H), 7.40 (m, 2 H), 7.68 (m, 1 H), 7.79 (m, 1 H)

후처리

  1. temperatureThe mixture was heated to 60° C. for 1.5 houes
  2. temperaturecooled
  3. customthe separated benzene layer was evaporated to dryness
  4. customthe crude purified via flash chromatography over silica
  5. dry with materialafter drying in vacuo the title compound (0.49 g, 15%)

출처 및 근거

ORD 기록
ord-fc1c58c04a2c403dacd0a0192753eb4f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456200B2

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