Hydrochloric Acid → Methyl 2-(6-methoxy-1H-inden-3-yl)butanoate

HRID 46016

反応式

HRID 46016 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2.Br[CH:14]([CH2:19][CH3:20])[C:15]([O:17][CH3:18])=[O:16].Cl>C1COCC1.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9]([C:8]([CH:14]([CH2:19][CH3:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH2:6]2)=[CH:10][CH:11]=1

参加物

6

反応物 3

HCID 313Hydrochloric Acid2 回HCID 787875-Methoxyindan-1-oneHCID 95577Butanoic acid, 2-bromo-, methyl ester

生成物 1

HCID 11402344Methyl 2-(6-methoxy-1H-inden-3-yl)butanoate収率 104.4%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

An oven dried 5-L four-necked round-bottomed flask was fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer. Under Ar protection, a suspension of 5-methoxy-1-indanone (80.0 g, 494 mmol), Zn powder (Lancaster, 56.2 g, 865 mmol) in 2 L anhydrous THF was stirred at 60° C. (internal temperature), while a solution of methyl bromobutyrate (134.1 g, 741 mmol) in 400 mL anhydrous THF was added slowly through an addition funnel. After completion of the addition, the reaction mixture was stirred at 60° C. (internal temperature) for 1 hour. The reaction was followed by TLC analysis of aliquots following 1N aqueous HCl work-up. After the reaction was completed, it was cooled in an ice-water bath followed by slow addition of 3 L of 1N HCl solution. The pot temperature was kept below 20° C. The mixture was then extracted with 1 L EtOAc. The organic layer was washed with water until pH 6.0-7.0, then saturated NaCl solution, and dried over Na2SO4. The product (127 g, >99%), a yellow oil, was obtained after solvent removal and drying under vacuum. 1H NMR (DMSO-d6) δ 7.28 (d, 1H), 7.05 (d, 1H), 6.82 (dd, 1H), 6.22 (s, 1H), 3.72 (s, 3H), 3.60 (m, 1H), 3.58 (s, 3H), 3.28 (s, 2H), 1.95 (m, 1H), 1.80 (m, 1H), 0.88 (t, 3H).

後処理

  1. dry with materialAn oven dried 5-L four-necked round-bottomed flask
  2. customwas fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer
  3. additionAfter completion of the addition
  4. stirringthe reaction mixture was stirred at 60° C. (internal temperature) for 1 hour
  5. temperatureit was cooled in an ice-water bath
  6. customwas kept below 20° C
  7. extractionThe mixture was then extracted with 1 L EtOAc
  8. washThe organic layer was washed with water until pH 6.0-7.0
  9. dry with materialsaturated NaCl solution, and dried over Na2SO4

出典と根拠

ORDレコード
ord-75d4465f86f5474e94ad47e3d1da022a
出典データセット
uspto-grants-2013_09
特許番号
US08541618B2

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