Hexane → (5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone

HRID 54870

반응식

HRID 54870 반응식
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][C@@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][C:10]2=[O:20])=[CH:5][CH:4]=1.B(Br)(Br)Br.CCCCCC>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:13][C@@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][C:10]2=[O:20])=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 8058HexaneHCID 25134Boron tribromideHCID 53894593(5R)-3-(4-methoxyphenyl)-5-phenyl-2-oxazolidinone

생성물 1

HCID 54314065(5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone수율 80.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

4.10 g (15.2 mM) of (5R)-3-(4-methoxyphenyl)-5-phenyl-2-oxazolidinone synthesized in Example 1 was dissolved in 100 ml of methylene chloride and cooled to -75° to 70° C. on a dry ice-acetone cooling bath. To the solution, 31.5 ml of 1.0M-solution of boron tribromide in methylene chloride was added dropwise in 43 minutes, followed by stirring for 1 hour at -75° to -70° C. and further stirring for 2 hours at room temperature. After the reaction, the reaction mixture was poured into ice water and subjected to extraction with ethyl acetate. The organic layer was washed with water and dried with anhydrous sodium sulfate, followed by evaporation under reduced pressure to obtain a residue. To the residue, an appropriate amount of hexane was added to precipitate a crystal. The crystal was recovered by filtration, thus obtaining 3.13 g of (5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone (Yield: 80.5%).

후처리

  1. temperaturecooled to -75° to 70° C. on a dry ice-acetone cooling bath
  2. stirringfurther stirring for 2 hours at room temperature
  3. customAfter the reaction
  4. extractionsubjected to extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customfollowed by evaporation under reduced pressure
  8. customto obtain a residue
  9. customto precipitate a crystal
  10. filtrationThe crystal was recovered by filtration

출처 및 근거

ORD 기록
ord-e2d2b1182e16479096182241bccfd947
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624600

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