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

HRID 1265279

반응식

HRID 1265279 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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=7.25 Hz), 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-da59cb7ec6fb47959699c69dc3e3fc1d
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545108B1

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