Aluminium lithium hydride → [2-(4-Bromo-phenyl)4-isopropyl-oxazol-5-yl]-methanol

HRID 490714

반응식

HRID 490714 반응식
C([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH:18]([CH3:20])[CH3:19])=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[O:10][C:6]([CH2:4][OH:3])=[C:7]([CH:18]([CH3:20])[CH3:19])[N:8]=2)=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 690532562-(4-Bromo-phenyl)4-isopropyl-oxazole-5-carboxylic acid ethyl ester

생성물 1

HCID 69056838[2-(4-Bromo-phenyl)4-isopropyl-oxazol-5-yl]-methanol수율 99.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-(4-bromo-phenyl)-4-isopropyl-oxazole-5-carboxylic acid ethyl ester (20.6 g, 60.9 mmol) in THF (300 mL) is cooled in an ice-water bath and treated portionwise with LiAlH4 (2.8 g, 73 mmol). The reaction is complete after 1.5 h. Ice chips (˜10 g) are added to quench the excess hydride reagent, and anhydrous Na2SO4 (˜50 g) is added. The thick suspension is stirred 30 min, filtered through celite, and washed with ThF (600 mL). The filtrate is dried (Na2SO4) and concentrated. The crude product is purified by silica gel flash chromatography using hexanes:ethyl acetate (3:1) to give a white solid (17.9 g, 99%).

후처리

  1. additionIce chips (˜10 g) are added
  2. customto quench the excess hydride reagent, and anhydrous Na2SO4 (˜50 g)
  3. additionis added
  4. filtrationfiltered through celite
  5. washwashed with ThF (600 mL)
  6. dry with materialThe filtrate is dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product is purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-00916f7c763b4ad4a606108189afe6e2
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528160B2

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