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

HRID 490716ノート

反応式

HRID 490716 の反応式
[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

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 858606262-(4-Bromo-phenyl)4-isopropyl-oxazole-5-carbaldehydeHCID 178418573HCID 178418573、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-82dfdae890274655b6ab6e259470ed3a
出典データセット
uspto-grants-2009_05
特許番号
US07528160B2

反応ノート

読み込み中…