Benzene → 9a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7826

反応式

HRID 7826 の反応式
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([CH3:19])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:20]C)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br.C1C=CC=CC=1>C(Cl)Cl>[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([CH3:19])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:20])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 241BenzeneHCID 25134Boron tribromideHCID 120457759a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 99652719a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 9a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (76 mg, 0.267 mmol) in anhydrous CH2Cl2 (2 mL) was placed under a nitrogen atmosphere, cooled in an ice bath, and stirred while 1M BBr3 in CH2Cl2 (0.80 mL, 0.80 mmol) was added by syringe. The cooling bath was removed and the mixture was stirred at room temperature for 2 hours. The mixture was partitioned between EtOAc (20 mL) and water (20 mL) containing 2N HCl (2 mL). The organic phase was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil. This material was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate using 5% MeOH in CH2Cl2 as the developing solvent. The product band was eluted with 10% MeOH in CH2Cl2 and the eluant evaporated under vacuum to give an oil which was lyophilized from benzene to afford 9a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

後処理

  1. temperaturecooled in an ice bath
  2. additionwas added by syringe
  3. customThe cooling bath was removed
  4. customThe mixture was partitioned between EtOAc (20 mL) and water (20 mL)
  5. additioncontaining 2N HCl (2 mL)
  6. washThe organic phase was washed with brine (10 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under vacuum to an oil
  10. customThis material was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
  11. washThe product band was eluted with 10% MeOH in CH2Cl2
  12. customthe eluant evaporated under vacuum
  13. customto give an oil which

出典と根拠

ORDレコード
ord-86276ff0e0a9422aa0299c840223781e
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

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