6-bromo-4-(phenylmethyl)-3,4-dihydro-2H-1,4-benzoxazine → (4-Benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-(5-bromo-2-isopropyl-phenyl)-methanol

HRID 72621ノート

反応式

HRID 72621 の反応式
[CH2:1]([N:8]1[C:13]2[CH:14]=[C:15](Br)[CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Br:24][C:25]1[CH:26]=[CH:27][C:28]([CH:33]([CH3:35])[CH3:34])=[C:29]([CH:32]=1)[CH:30]=[O:31]>C1COCC1>[CH2:1]([N:8]1[C:13]2[CH:14]=[C:15]([CH:30]([C:29]3[CH:32]=[C:25]([Br:24])[CH:26]=[CH:27][C:28]=3[CH:33]([CH3:35])[CH3:34])[OH:31])[CH:16]=[CH:17][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 583408326-bromo-4-(phenylmethyl)-3,4-dihydro-2H-1,4-benzoxazineHCID 583408355-Bromo-2-isopropylbenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 67117055(4-Benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-(5-bromo-2-isopropyl-phenyl)-methanol収率 58.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-Benzyl-6-bromo-3,4-dihydro-2H-benzo[1,4]oxazine (1.5 g, 4.93 mmol) in THF (20 mL) was added 1.6 M n-butyl lithium in hexanes (3.0 mL, 74.93 mmol) at −78° C. The reaction was stirred for 30 min. then transferred to a stirred solution of 5-bromo-2-isopropylbenzaldehyde (1.12 g, 4.93 mmol) in THF (15 mL) at −78° C. After stirring for 30 min, the reaction was quenched by the addition of saturated aqueous solution of ammonium chloride. The resulting mixture was extracted with ethyl acetate (3×30 mL), and the combined organic layers were washed with water (25 mL) and brine (25 mL), then dried over sodium sulfate, concentrated and purified using neutral alumina column chromatography to give (4-Benzyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-(5-bromo-2-isopropyl-phenyl)-methanol (1.3 g).

後処理

  1. stirringAfter stirring for 30 min
  2. customthe reaction was quenched by the addition of saturated aqueous solution of ammonium chloride
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
  4. washthe combined organic layers were washed with water (25 mL) and brine (25 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified

出典と根拠

ORDレコード
ord-2f135918e3a34345b80b69ec1f6164fe
出典データセット
uspto-grants-2014_09
特許番号
US08828951B2

反応ノート

読み込み中…