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

HRID 273143ノート

反応式

HRID 273143 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 313Hydrochloric Acid溶媒

反応条件

温度
0 °C

実験手順

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)

後処理

  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%)

出典と根拠

ORDレコード
ord-fc1c58c04a2c403dacd0a0192753eb4f
出典データセット
uspto-grants-2008_11
特許番号
US07456200B2

反応ノート

読み込み中…