1-Iodooctane → (5R)-3-(4-octyloxyphenyl)-5-phenyl-2-oxazolidinone

HRID 54871

반응식

HRID 54871 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]2=[O:19])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C=O)C>[CH2:23]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]2=[O:19])=[CH:6][CH:7]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

참가 물질

5

반응물 3

HCID 123801-IodooctaneHCID 24758Sodium hydrideHCID 54314065(5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone

생성물 1

HCID 53637929(5R)-3-(4-octyloxyphenyl)-5-phenyl-2-oxazolidinone수율 30.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Then, 0.30 g (1.18 mM) of (5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone and 4.6 ml of DMF were placed in 30 ml-round bottomed flask, followed by stirring to form a solution. To the solution, 0.053 g (1.33 mM) of 60%-oily sodium hydride was added under stirring at room temperature. After the settlement of foaming, 0.25 ml (1.38 mM) of 1-iodooctane was added to the mixture, followed by stirring for 30 minutes on an oil bath kept at about 70° C. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by purification by silica gel column chromatography (eluent: toluene/ethyl acetate =100/1) and recrystallization from a toluene-methanol mixture solvent to obtain 0.13 g of (5R)-3-(4-octyloxyphenyl)-5-phenyl-2-oxazolidinone (Yield: 30.1%).

후처리

  1. customto form a solution
  2. stirringunder stirring at room temperature
  3. stirringby stirring for 30 minutes on an oil bath
  4. customkept at about 70° C
  5. customAfter the reaction
  6. customto precipitate a crystal
  7. filtrationThe crystal was recovered by filtration
  8. washwashed with water
  9. customfollowed by purification by silica gel column chromatography (eluent: toluene/ethyl acetate =100/1) and recrystallization from a toluene-methanol mixture solvent

출처 및 근거

ORD 기록
ord-ccc751841a9b4b238bdcd8e8f959367b
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624600

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