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

HRID 7884

反応式

HRID 7884 の反応式
[C:1]([C:4]1[C:5](=[O:24])[CH2:6][CH2:7][C:8]2([CH2:20][CH2:21][CH2:22][CH3:23])[C:16]=1[C:15]1[C:10](=[C:11]([Cl:19])[C:12]([O:17]C)=[CH:13][CH:14]=1)[CH2:9]2)(=[O:3])[CH3:2].Cl.N1C=CC=CC=1>>[C:1]([C:4]1[C:5](=[O:24])[CH2:6][CH2:7][C:8]2([CH2:20][CH2:21][CH2:22][CH3:23])[C:16]=1[C:15]1[C:10](=[C:11]([Cl:19])[C:12]([OH:17])=[CH:13][CH:14]=1)[CH2:9]2)(=[O:3])[CH3:2]

参加物

3

反応物 2

HCID 10176127Pyridinium chlorideHCID 219908794-acetyl-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 99455194-acetyl-9a-butyl-8-chloro-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

反応条件

温度
200 °C

実験手順

A mixture of 4-acetyl-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (54 mg) and pyridine hydrochloride (3.5 g) was heated in an oil bath at 200° C. for one hour. After cooling to room temperature, the mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (32 mg). The crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 5% MeOH in CH2Cl2. The product band was eluted with 10% MeOH in CH2Cl2, the eluant evaporated under vacuum, and the residue lyophilized from benzene to afford 4-acetyl-9a-butyl-8-chloro-7-hydroxy-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 (50 mL) and water (50 mL)
  3. washThe organic phase was washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to an oil (32 mg)
  7. customThe crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
  8. washThe product band was eluted with 10% MeOH in CH2Cl2
  9. customthe eluant evaporated under vacuum

出典と根拠

ORDレコード
ord-49e41638e01341c08bfbc41dd6e4affb
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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