Acetophenone → HCID 67384805, compound

HRID 1471917Notes

Reaction equation

HRID 1471917 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:20][O:21][CH2:22][CH2:23][C:24](Cl)=O.O.[NH2:28][NH2:29]>C1(C)C=CC=CC=1.CCO.CC(O)=O>[CH3:20][O:21][CH2:22][CH2:23][C:24]1[NH:29][N:28]=[C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:2]=1

Participants

8

Reactant 4

HCID 7410AcetophenoneHCID 24654Hydrazine hydrate (1:1)HCID 2733832Lithium HexamethyldisilazideHCID 27597283-Methoxypropanoyl chloride

Product 1

HCID 67384805HCID 67384805, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of acetophenone (3.5 g, 29.1 mmol) in dry toluene (10 mL) was added LiHMDS (1.0 M in toluene) via syringe at 0° C. under argon. After 5 min, 3-methoxypropanoyl chloride (3.57 g, 29.1 mmol) was added in one portion via syringe. The ice bath was removed and AcOH (2 mL), EtOH (100 mL), and hydrazine hydrate (4.37 g, 87 mmol) were added. The reaction was refluxed for 2 h, cooled to room temperature, and concentrated. The residue was extracted with EtOAc/H2O, washed with brine, dried over MgSO4, and concentrated. The resulting residue was purified by silica gel column chromatography to give the title compound as pale yellow oil (2.0 g). LCMS m/z=203.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.85 (bs, 2H), 3.27 (s, 3H), 3.59 (t, J=6.82 Hz, 2H), 6.49 (s, 1H), 7.21-7.46 (m, 3H), 7.74 (m, 2H), 12.56 (s, 1H).

Workup

  1. customThe ice bath was removed
  2. temperatureThe reaction was refluxed for 2 h
  3. concentrationconcentrated
  4. extractionThe residue was extracted with EtOAc/H2O
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-07dc023b8f5346e99448d109e4f8cb1d
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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