6-Oxabicyclo[3.1.0]hexane → 6-cyano-3,4-dihydro-2,2-dimethyl-4-(2-hydroxycyclopentan-1-yl)-2H-1,4-benzoxazine

HRID 37119

반응식

HRID 37119 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][NH:8][C:7]=2[CH:14]=1)#[N:2].[H-].[Na+].[CH:17]12[O:22][CH:18]1[CH2:19][CH2:20][CH2:21]2>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[CH2:9][N:8]([CH:17]3[CH2:21][CH2:20][CH2:19][CH:18]3[OH:22])[C:7]=2[CH:14]=1)#[N:2]

참가 물질

6

반응물 3

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 24758Sodium hydrideHCID 105356226-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine

생성물 1

HCID 199345646-cyano-3,4-dihydro-2,2-dimethyl-4-(2-hydroxycyclopentan-1-yl)-2H-1,4-benzoxazine

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

In 20 ml of N,N-dimethylformamide was dissolved 1.0 g of 6-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine followed by addition of 0.24 g of sodium hydride. The mixture was stirred at 70° C. for 1 hour and after cooling to room temperature, 0.5 ml of cyclopentene oxide was added. The mixture was stirred at 70° C. for 3 hours. The reaction mixture was then allowed to cool, diluted with water and extracted with ethyl acetate. The extract was washed with water and aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography and the resulting crude crystals were recrystallized from ethyl acetate-hexane to give 0.53 g of 6-cyano-3,4-dihydro-4-(2-hydroxycyclopentan-1-yl)-2,2-dimethyl-2H-1,4-benzoxazine.

후처리

  1. temperatureafter cooling to room temperature
  2. stirringThe mixture was stirred at 70° C. for 3 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography
  9. customthe resulting crude crystals were recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-658be5a07e2c441eb1bd87c04cd5b359
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420126

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