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 72621노트

반응식

HRID 72621 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2f135918e3a34345b80b69ec1f6164fe
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828951B2

반응 노트

불러오는 중…