Water → HCID 67795169, compound

HRID 653829Notes

Reaction equation

HRID 653829 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:24][N:25]1[C:29]([C:30](=O)[C:31]([O:33][CH3:34])=[O:32])=[C:28]([O:36][CH2:37][C:38]2[N:39]=[C:40]([CH3:43])[S:41][CH:42]=2)[C:27]([CH3:44])=[N:26]1.O>C1COCC1.CCCCCC>[CH3:24][N:25]1[C:29](/[C:30](=[CH:2]\[O:3][CH3:4])/[C:31]([O:33][CH3:34])=[O:32])=[C:28]([O:36][CH2:37][C:38]2[N:39]=[C:40]([CH3:43])[S:41][CH:42]=2)[C:27]([CH3:44])=[N:26]1

Participants

6

Reactant 3

HCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 54483453HCID 54483453, compound

Product 1

HCID 67795169HCID 67795169, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a suspension of methoxymethyltriphenylphosphonium chloride (2 g, 5.84 mmol) in anhyrous THF was added 3.5 ml solution of lithium n-butylate (1.6 mol) in hexane. After stirring at room temperature for 30 minutes, methyl {1,3-dimethyl-4-[1-(2-methylthiazol-4-yl)methyloxy]pyrazol-5-yl}glyoxalate (0.6 g, 1.95 mmol) in anhydrous THF (6 ml) was added thereto and the mixture was allowed to stand for two hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed over silica gel to obtain (E)-methyl 2-{1,3-dimethyl-4-[1-(2-methylthiazol-4-yl)methyloxy]pyrazol-5-yl}-3-methoxyacrylate (compound No. 9 in Table 1) as an oil (0.25 g, 38.1%).

Workup

  1. waitto stand for two hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-9bdb978d585f4e4c898f876e6b1975c1
Source dataset
uspto-grants-1992_07
Patent number
US05128481

Reaction notes

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