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

HRID 1995111ノート

反応式

HRID 1995111 の反応式
[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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride3 回HCID 12853039HCID 12853039、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0ddacd702941498a83fd5f2e1fc5cafd
出典データセット
uspto-grants-1983_09
特許番号
US04402973

反応ノート

読み込み中…