2-Butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone → 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7856

反応式

HRID 7856 の反応式
[CH2:1]([C:5]1([CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH3:22])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[Cl:14])[C:6]1=O)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.Cl.CCOC(C)=O>[CH2:1]([C:5]12[CH2:18][CH2:19][C:20](=[O:23])[C:21]([CH3:22])=[C:6]1[C:7]1[C:12](=[C:11]([Cl:14])[C:10]([O:15][CH3:16])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 1

HCID 219909112-Butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone

生成物 1

HCID 219908769a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one収率 60.6%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A solution of 2-butyl-4-chloro-5-methoxy-2-(3-oxo-pentyl)-1-indanone (250 mg, 0.74 mmol) in acetic acid (2 mL) was diluted with 6N aqueous HCl (2 mL). The resulting mixture was stirred and heated in an oil bath at 90° C. for 18 hours, then kept at room temperature for 2 days. The mixture was diluted with EtOAc (20 mL), washed with water (30 mL), 5% NaHCO3 (10 mL) and brine (5 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (250 mg). The crude product was purified by preparative layer chromatography on three 0.1×20×20 silica gel GF plates, developing with 5% EtOAc in CH2Cl2, to afford 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (143 mg).

後処理

  1. washwashed with water (30 mL), 5% NaHCO3 (10 mL) and brine (5 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum to an oil (250 mg)
  5. customThe crude product was purified by preparative layer chromatography on three 0.1×20×20 silica gel GF plates

出典と根拠

ORDレコード
ord-6121252028114c99b582eb81c90945f8
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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