Hydrochloric Acid → 2'-Fluoro-5-methyl-1,2,3,6-tetrahydro[1,1'-biphenyl]-3-ol

HRID 485530노트

반응식

HRID 485530 반응식
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][C:14](=[O:16])[CH:13]=[C:12]([CH3:17])[CH2:11]1.Cl>C(O)C>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH:14]([OH:16])[CH:13]=[C:12]([CH3:17])[CH2:11]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride3회HCID 12853039HCID 12853039, 화합물

생성물 1

HCID 128530402'-Fluoro-5-methyl-1,2,3,6-tetrahydro[1,1'-biphenyl]-3-ol수율 95.1%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a stirred mixture of sodium borohydride (2.0 g, 0.05 mole) in 400 ml of ethanol was added in one portion 5-(2-fluorophenyl)-3-methyl-2-cyclohexen-1-one (42.3 g, 0.21 mole) in 50 ml of ethanol. The reaction mixture was heated under reflux for 16 hours. An additional 2.0 g of sodium borohydride was then added to the reaction mixture and heating under reflux continued for an additional 2 hours. Again, 2.0 g of sodium borohydride was added to the reaction mixture and heating under reflux continued for a 2 hour period. The reaction mixture was stirred with ice, then acidified with aqueous 10% hydrochloric acid. The mixture was extracted with diethyl ether, and the ether extract was washed with an aqueous solution saturated with sodium bicarbonate. The organic layer was dried with sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 5-(2-fluorophenyl)-3-methyl-2-cyclohexen-1-ol (41.2 g) as an oil.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. temperatureheating
  6. temperatureunder reflux
  7. waitcontinued for a 2 hour period
  8. extractionThe mixture was extracted with diethyl ether
  9. extractionthe ether extract
  10. washwas washed with an aqueous solution saturated with sodium bicarbonate
  11. dry with materialThe organic layer was dried with sodium sulfate
  12. filtrationfiltered
  13. customThe filtrate was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-945aedd8443849849ac18bec54c8b1f1
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04536591

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