Water → HCID 17830179, compound

HRID 1172582Notes

Reaction equation

HRID 1172582 reaction equation
[CH2:1]([N:3]1[C:7]([CH:8]2C(=O)O[C:11](C)(C)[O:10][C:9]2=[O:17])=[CH:6][C:5]([CH3:18])=[N:4]1)[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.O.C(N(CC)CC)C>CO>[CH3:11][O:10][C:9](=[O:17])[CH2:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([CH3:18])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 59556302HCID 59556302, compound

Product 1

HCID 17830179HCID 17830179, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

5-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-2,2-dimethyl-[1,3]dioxane-4,6-dione (11.05 g, 43.8 mmol) was dissolved in anhydrous methanol (125 ml) followed by the addition of p-TsOH×H2O (36.68 g, 192.85 mmol). The resulting reaction mixture was heated to 60° C. for 75 minutes, cooled to 0° C. and triethylamine (26.85 ml, 192.9 mmol) was added drop by drop over a period of 20 minutes. The resulting mixture was concentrated under reduced pressure. The residue was taken into DCM (200 ml) and washed with water (2×75 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silicagel, DCM/methanol=30/1) to give 5.56 g (70%) of (2-ethyl-5-methyl-2H-pyrazol-3-yl)-acetic acid methyl ester. LC-MS: tR 0.62 min; [M+H]+=183.18.

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to 0° C.
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. washwashed with water (2×75 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography (silicagel, DCM/methanol=30/1)

Sources & evidence

ORD record
ord-3ea2674515f142b58ae9fbcc2ad556b8
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

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