Diisobutylaluminum hydride → (5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

HRID 250222노트

반응식

HRID 250222 반응식
C[O:2][C:3]([C:5]1[C:6]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])=[N:7][O:8][C:9]=1[CH:10]1[CH2:12][CH2:11]1)=O.CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1>[CH:10]1([C:9]2[O:8][N:7]=[C:6]([C:13]3[C:14]([Cl:20])=[CH:15][CH:16]=[CH:17][C:18]=3[Cl:19])[C:5]=2[CH2:3][OH:2])[CH2:12][CH2:11]1

참가 물질

5

반응물 2

HCID 14487Diisobutylaluminum hydride2회HCID 53421832Methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole-4-carboxylate

생성물 1

HCID 45790382(5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol수율 93%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a 0° C. solution of 5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole-4-carboxylic acid methyl ester (0.80 g, 2.6 mmol) in THF (8 mL) is added a 1M DIBAL solution in toluene (5.66 mL). The reaction is stirred one hour. An additional 1M DIBAL solution in Toluene (5.66 mL) is added and the reaction is stirred for an additional hour. The reaction is quenched with methanol and is acidified with aqueous HCl solution (1M). The aqueous solution is extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure to yield the title compound (0.68 g, 93%). ES/MS m/e 284.0 (M+1).

후처리

  1. stirringthe reaction is stirred for an additional hour
  2. customThe reaction is quenched with methanol
  3. extractionThe aqueous solution is extracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure

출처 및 근거

ORD 기록
ord-0fe56a33907240fda7b6055c5eedf1a7
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863302B2

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