Pyridinium chloride → 9a-[(1E)-1-butenyl]-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7830

反応式

HRID 7830 の反応式
[CH: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)=[CH:2]\[CH2:3][CH3:4].Cl.N1C=CC=CC=1>>[CH: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)=[CH:2]\[CH2:3][CH3:4]

参加物

3

反応物 2

HCID 10176127Pyridinium chlorideHCID 219908999a-[(1E)-1-butenyl]-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 98785179a-[(1E)-1-butenyl]-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

反応条件

温度
190 °C

実験手順

A mixture of 9a-[(1E)-1-butenyl]-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (31.7 mg, 0.112 mmol) and pyridine hydrochloride (384 mg, 3.32 mmol) was placed under a nitrogen atmosphere and heated in an oil bath at 190° C. for 65 minutes. After cooling to room temperature, the reaction mixture was partitioned between water (4 ml) and EtOAc (10 mL). The organic phase was recovered, washed with brine (5 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (30 mg). The crude product was purified by silica gel chromatography on a Biotage FLASH 12S column (1.2×7.5 cm), eluting with 3:1 hexanes-EtOAc. The product containing fractions were concentrated under vacuum and the residue lyophilized from benzene to provide 9a-[(1E)-1-butenyl]-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a yellow, amorphous solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between water (4 ml) and EtOAc (10 mL)
  3. customThe organic phase was recovered
  4. washwashed with brine (5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum to an oil (30 mg)
  8. customThe crude product was purified by silica gel chromatography on a Biotage FLASH 12S column (1.2×7.5 cm)
  9. washeluting with 3:1 hexanes-EtOAc
  10. additionThe product containing fractions
  11. concentrationwere concentrated under vacuum

出典と根拠

ORDレコード
ord-d7b694b1a63448cfb05ba1ccd587d001
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

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