Acetic Acid → HCID 21990921、化合物

HRID 7832ノート

反応式

HRID 7832 の反応式
[CH2:1]([C:5]1([CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=O)[CH2:2][CH2:3][CH3:4].N1CCCC1.C(O)(=O)C>>[CH2:1]([C:5]12[CH2:17][CH2:18][C:19](=[O:21])[CH:20]=[C:6]1[C:7]1[C:12](=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 219908542-Butyl-5-methoxy-2-(3-oxo-butyl)-1-indanone

生成物 1

HCID 21990921HCID 21990921、化合物

反応条件

温度
60 °C

実験手順

The solution from step 2 was treated with pyrrolidine (6.9 mL, 82 mmol) and acetic acid (4.7 mL, 82 mmol), placed under a nitrogen atmosphere, and stirred with heating in a 60° C. bath for 22 hours. After cooling to room temperature, the reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL). The EtOAc phase was washed with 0.8N HCl (500 mL), water (500 mL), 5% NaHCO3 (500 mL), and brine (200 mL), dried with MgSO4, filtered, and evaporated under vacuum to a brown oil (22.8 g). This material was purified by column chromatography on EM silica gel 60 (230-400 mesh, 684 g), using 5% EtOAc in CH2Cl2 as eluting solvent, to afford 9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (11.2 g) as a solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL)
  3. washThe EtOAc phase was washed with 0.8N HCl (500 mL), water (500 mL), 5% NaHCO3 (500 mL), and brine (200 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to a brown oil (22.8 g)
  7. customThis material was purified by column chromatography on EM silica gel 60 (230-400 mesh, 684 g)
  8. washas eluting solvent

出典と根拠

ORDレコード
ord-6eb19596dc4f425b98b352cad4d4b671
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

反応ノート

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