Ammonium Chloride → 1-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol

HRID 490716노트

반응식

HRID 490716 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH:16]=[O:17])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.[CH3:18][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH:16]([OH:17])[CH3:18])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 858606262-(4-Bromo-phenyl)4-isopropyl-oxazole-5-carbaldehydeHCID 178418573HCID 178418573, 화합물2회

생성물 1

HCID 587656641-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol수율 63%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-(4-bromo-phenyl)-4-isopropyl-oxazole-5-carbaldehyde (14.4 g, 84.9 mmol) in THF (300 mL) is cooled to −78° C. and treated dropwise with methyl magnesium bromide (25 mL, 75 mmol, 3M Et2O). After 1 h, more methyl magnesium bromide (12 mL, 36 mmol) is added. The reaction mixture is stirred 1.5 h, and saturated NH4Cl solution (10 ml) is added dropwise. The mixture is partitioned between saturated NH4Cl solution (10 ml), 1N HCl (25 mL), and Et2O (300 mL). The organic layer is washed with brine (150 mL), dried (Na2SO4), and concentrated. The crude product is purified by silica gel flash chromatography using hexanes:ethyl acetate (9:1 to 5:1) to give an offwhite solid (9.5 g, 63%).

후처리

  1. customThe mixture is partitioned between saturated NH4Cl solution (10 ml), 1N HCl (25 mL), and Et2O (300 mL)
  2. washThe organic layer is washed with brine (150 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-82dfdae890274655b6ab6e259470ed3a
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528160B2

반응 노트

불러오는 중…