Aluminium lithium hydride → [5-(3-Chlorophenyl)isoxazol-3-yl]methanol

HRID 732119노트

반응식

HRID 732119 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[O:14][N:13]=1)=O)C>C1COCC1>[Cl:23][C:19]1[CH:18]=[C:17]([C:15]2[O:14][N:13]=[C:12]([CH2:10][OH:9])[CH:16]=2)[CH:22]=[CH:21][CH:20]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 46929188Ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate

생성물 1

HCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanol수율 79.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium aluminum hydride (320 mg, 8.4 mmol) was slowly added to a solution of 5-(3-chloro-phenyl)-isoxazole-3-carboxylic acid ethyl ester (2.0 g, 8.4) in THF (100 ml) at r.t After 1 h, the reaction mixture was quenched with water and then extracted with EA. The organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The resulting residue was then purified by column chromatography using 15-40% EA in hex. to afford the title compound (1.32 g, 75%,). 1H NMR: 7.78 (s, 1H), 7.68 (m, 1H), 7.43 (m, 2H), 6.63 (s, 1H), 4.84 (d, 2H), 2.23 (t, 1H).

후처리

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with EA
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was then purified by column chromatography

출처 및 근거

ORD 기록
ord-eb43f023bf204498996acd380a13cc79
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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