Ethyl Acetate → HCID 178448753, compound

HRID 1726932Notes

Reaction equation

HRID 1726932 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH2:10]([N:14]1[C:19](=[O:20])[CH:18]=[N:17][C:16]([CH3:21])=[N:15]1)[CH2:11][CH2:12][CH3:13].[NH4+].[Cl-].C(OCC)(=O)C>CCOCC>[CH2:10]([N:14]1[C:19](=[O:20])[CH:18]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[NH:17][C:16]([CH3:21])=[N:15]1)[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 68963075HCID 68963075, compoundHCID 178418370HCID 178418370, compound

Product 1

HCID 178448753HCID 178448753, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Methylphenylmagnesium bromide (1.64 mL, 1.0 M in ether) was added all at once via syringe to a well-stirred solution of 1-n-butyl-3-methyl-1,2,4-triazin-6-one (178 mg, 1.06 mmol) in ether (9.85 mL) under N2 at room temperature. After stirring the resulting mixture overnight, saturated aqueous NH4Cl (10 mL) and ethyl acetate (10 mL) were added, the organic phase was separated, and the aqueous layer was extracted once more with ethyl acetate. The combined organic layers were dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel (5 g, 4:1 hexanes:ethyl acetate) to afford Compound 22 as a tan solid (236 mg, 86% yield).

Workup

  1. additionwere added
  2. customthe organic phase was separated
  3. extractionthe aqueous layer was extracted once more with ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography on silica gel (5 g, 4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-dbfd02af5abf4944aad8f9d3426084dd
Source dataset
uspto-grants-2009_02
Patent number
US07494996B2

Reaction notes

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