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

HRID 7886

反応式

HRID 7886 の反応式
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]#[N:20])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:23])[C:9]([O:21]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]([C:19]#[N:20])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:23])[C:9]([OH:21])=[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 219908869a-butyl-8-chloro-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 99666859a-butyl-8-chloro-4-cyano-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 9a-butyl-8-chloro-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (65 mg) and pyridine hydrochloride (4.2 g) was heated in an oil bath at 200° C. for 85 minutes. 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. The residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates, developing with 5% MeOH in CH2Cl2. The product bands were eluted with 10% MeOH in CH2Cl2, the eluant evaporated under vacuum, and the residue lyophilized from benzene (3 mL) plus EtOH (0.1 mL) to afford 9a-butyl-8-chloro-4-cyano-7-hydroxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous yellow 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
  7. customThe residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates
  8. washThe product bands were eluted with 10% MeOH in CH2Cl2
  9. customthe eluant evaporated under vacuum

出典と根拠

ORDレコード
ord-4492a1316c2143eaaae289f2e539a4d5
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

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