Methanol, magnesium salt (2:1) → HCID 72357170, compound

HRID 505936Notes

Reaction equation

HRID 505936 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[O:6]C(=O)[CH:4]=1.[CH3:14][O-:15].[Mg+2].[CH3:17][O-:18]>>[F:10][C:9]([F:11])([F:12])[C:7](=[O:6])[CH2:8][C:3]([O:2][CH3:1])=[CH:4][C:14]([O:18][CH3:17])=[O:15]

Participants

3

Reactant 2

HCID 164537Methanol, magnesium salt (2:1)HCID 68743481HCID 68743481, compound

Product 1

HCID 72357170HCID 72357170, compoundYield 82.5%

Procedure

A solution of 4-methoxy-6-trifluoromethylpyran-2-one (2.7 g, 14 mmol) in a methanolic magnesium methanolate solution (8.5% Mg(OMe)2, 8.36 g, 8 mmol) was heated under reflux for 16 hours. The solution was concentrated and taken up in water and ethyl acetate, and the organic phase was brought to pH 5 by adding dilute hydrochloric acid. The organic phase was separated off, dried and concentrated. 1.5 g of crude product were obtained as a yellow oil. Kugelrohr distillation at 0.04 mbar and about 160° C. afforded methyl 6,6,6-trifluoro-3-methoxy-5-oxo-2-hexenoate (1.50 g, 6.6 mmol, 48%) as a pale yellow oil.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationThe solution was concentrated
  3. additionby adding dilute hydrochloric acid
  4. customThe organic phase was separated off
  5. customdried
  6. concentrationconcentrated
  7. custom1.5 g of crude product were obtained as a yellow oil
  8. distillationKugelrohr distillation at 0.04 mbar and about 160° C.

Sources & evidence

ORD record
ord-c4ccbac518d24c90a29bab27b9747206
Source dataset
uspto-grants-2010_08
Patent number
US07781601B2

Reaction notes

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