Pyridinium chloride → 9a-butyl-8-chloro-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7857

反応式

HRID 7857 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](=[C:8]([Cl:22])[C:9]([O:20]C)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1>>[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](=[C:8]([Cl:22])[C:9]([OH:20])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

参加物

3

反応物 2

HCID 10176127Pyridinium chlorideHCID 219908769a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 99010879a-butyl-8-chloro-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

反応条件

温度
195 °C

実験手順

A mixture of 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (36.6 mg) and pyridine hydrochloride (2.66) was stirred and heated in an oil bath at 190-200° C. for 80 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (20 mL) and water (30 mL). The organic phase was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 10% EtOAc in CH2Cl2. The UV visible product band was eluted with EtOAc, the eluant evaporated under vacuum, and the residue lyophilized from benzene to afford 9a-butyl-8-chloro-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between EtOAc (20 mL) and water (30 mL)
  3. washThe organic phase was washed with brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
  8. washThe UV visible product band was eluted with EtOAc
  9. customthe eluant evaporated under vacuum

出典と根拠

ORDレコード
ord-e71cb2ebf2654d4ba5d844ad5a953bf8
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

関連ノート

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