Ethyl Acetate → (6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide

HRID 1295945노트

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HRID 1295945 반응식
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]#[N:10].[C:11]([C:15]1[C:24]2[O:23][CH2:22][CH2:21][NH:20][C:19]=2[CH:18]=[C:17]([C:25](=[O:27])[CH3:26])[CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C(OCC)(=O)C>CN(C)C=O>[C:25]([C:17]1[CH:16]=[C:15]([C:11]([CH3:14])([CH3:12])[CH3:13])[C:24]2[O:23][CH2:22][CH2:21][N:20]([CH2:8][C:9]#[N:10])[C:19]=2[CH:18]=1)(=[O:27])[CH3:26]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 589099341-[8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

생성물 1

HCID 22930164(6-acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-4-yl]methyl cyanide수율 99.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

Potassium carbonate (3.6 g, 26 mmol) and bromoacetonitrile (15.4 g, 128.6 mmol) were added to a solution of 1-[8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone (6.0 g, 25.5 mmol) in dimethylformamide (100 ml) and the mixture was stirred at 90° C. for 6 hours. Ethyl acetate was added, the reaction mixture was washed with water and brine in that order and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (6.9 g) as a light yellow oil.

후처리

  1. washthe reaction mixture was washed with water and brine in that order
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-8d087dac437c456c90fa4b3cda795f08
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244730B2

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