Water → HCID 28896399, compound

HRID 878526Notes

Reaction equation

HRID 878526 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.O.C([O:16][C:17](=O)[CH2:18][CH3:19])C>>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH2:11][C:17](=[O:16])[CH2:18][CH3:19])=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 962WaterHCID 7749Ethyl PropionateHCID 8500p-METHYLACETOPHENONEHCID 24758Sodium hydride

Product 1

HCID 28896399HCID 28896399, compoundYield 52%

Procedure

To a suspension of NaH (60%, 106 mg, 4.44 mmol) in 2 mL propionic acid ethyl ester was added 1-(4-methylphenyl)ethanone (500 mg, 3.7 mmol) at 0-5° C. The reaction mixture was stirred overnight at rt. Water was added, and the mixture was extracted with EtOAc (3×50 mL). The organic layers were washed with brine, dried over Na2SO4, and concentrated to dryness. The residue was purified by flash column chromatography (PE/EtOAc=10/1) to give the title compound (370 mg, 52%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.22 (3H, m), 2.45 (5H, m), 6.17 (2H, s), 7.27 (2H, d, J=10 Hz), 7.81 (2H, d, J=11.2 Hz). [M+H] Calc'd for C12H14O2, 191; Found, 191.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×50 mL)
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash column chromatography (PE/EtOAc=10/1)

Sources & evidence

ORD record
ord-9d771a1acf324e24871515e45409f733
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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