Sodium hydride → 2-(Naphthalene-1-carbonyl)4-oxo-4-phenyl-butyric acid ethyl ester

HRID 411125

反応式

HRID 411125 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:20])[CH2:7][C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)=[O:9])[CH3:4]>C1(C)C=CC=CC=1>[CH2:3]([O:5][C:6](=[O:20])[CH:7]([C:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)=[O:9])[CH2:7][C:8](=[O:9])[C:10]1[CH:19]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:4]

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 2760157Ethyl 3-(naphthalen-8-yl)-3-oxopropanoate

生成物 1

HCID 205827512-(Naphthalene-1-carbonyl)4-oxo-4-phenyl-butyric acid ethyl ester収率 99.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A suspension of NaH (60% in mineral oil, 323 mg, 8.07 mmol) in toluene (20 mL) was treated with 3-Naphthalen-1-yl-3-oxo-propionic acid ethyl ester (1.63 g, 6.7 mmol). The resulting suspension was stirred at rt under Ar for 1 h, then treated with 2-bromocetophenone (1.61 g, 8.07 mmol). The suspension was immersed in a 70° C. oil bath and stirred under Ar for 4 h, cooled to rt, diluted with toluene and washed with H2O and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography (SiO2, 10-20% EtOAc/Heptane) to afford 2-(Naphthalene-1-carbonyl)-4-oxo-4-phenyl-butyric acid ethyl ester (1.2 g) contaminated with a small amount of unidentified aromatic impurity: 11H NMR (CDCl3, chemical shifts in ppm relative to TMS): 1.03 (t, 3H, J=7.25Hz), 3.72 (dd, 1H, J=18.8 Hz, J=5.4 Hz), 3.96 (dd, 1H, J=18.8 Hz, J=8.05 Hz), 4.09 (m, 2H), 5.16 (m, 1H), 7.45-7.63 (m, 6H), 7.88 (d, 1H, J=7.9 Hz), 8.0-8.07 (m, 3H), 8.24 (d, 1H, J=7.2 Hz)), 8,48 (d, 1H, J=8.7 Hz).

後処理

  1. customwas immersed in a 70° C.
  2. stirringstirred under Ar for 4 h
  3. temperaturecooled to rt
  4. washwashed with H2O and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash chromatography (SiO2, 10-20% EtOAc/Heptane)

出典と根拠

ORDレコード
ord-060671d0a7144da49f9fd9c5d68e30f3
出典データセット
uspto-grants-2003_05
特許番号
US06559091B1

関連ノート

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