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

HRID 1265279Notes

Reaction equation

HRID 1265279 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-da59cb7ec6fb47959699c69dc3e3fc1d
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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