Acetic Acid → 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7848

反応式

HRID 7848 の反応式
[CH2:1]([C:5]1([CH2:18][CH2:19][C:20](=[O:22])[CH3:21])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[CH3:14])[C:6]1=O)[CH2:2][CH2:3][CH3:4].C(O)(=O)C.N1CCCC1>C1(C)C=CC=CC=1.CCOCC>[CH2:1]([C:5]12[CH2:18][CH2:19][C:20](=[O:22])[CH:21]=[C:6]1[C:7]1[C:12](=[C:11]([CH3:14])[C:10]([O:15][CH3:16])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 219908922-Butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone

生成物 1

HCID 219908849a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one収率 55.5%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

A solution of impure 2-butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone (0.96 g, 3.17 mmol), acetic acid (0.182 mL, 3.18 mmol) and pyrrolidine (0.265 mL, 3.18 mmol) in anhydrous toluene (15.9 mL) was stirred and heated in an oil bath at 80° C. for 16 hours. After cooling, the reaction mixture was diluted with Et2O (100 mL), washed with 1N HCl (2×25 mL), 5% NaHCO3 (50 mL), and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to a dark brown oil (0.86 g). The crude product was purified by chromatography on a Biotage FLASH 40S column, eluting with 9:1 hexanes-EtOAc, to afford 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.50 g) as an off-white solid.

後処理

  1. temperatureAfter cooling
  2. washwashed with 1N HCl (2×25 mL), 5% NaHCO3 (50 mL), and brine (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum to a dark brown oil (0.86 g)
  6. customThe crude product was purified by chromatography on a Biotage FLASH 40S column
  7. washeluting with 9:1 hexanes-EtOAc

出典と根拠

ORDレコード
ord-c4d098d6e0c64655809c3a2af90167be
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

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