5-(2-Fluoro-3-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → HCID 57705536, compound

HRID 1662503Notes

Reaction equation

HRID 1662503 reaction equation
[F:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]=[C:5]1[C:10](=[O:11])[O:9][C:8]([CH3:13])([CH3:12])[O:7][C:6]1=[O:14].[CH2:21]([Mg]Br)[CH3:22]>C1COCC1>[F:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]([CH:5]1[C:6](=[O:14])[O:7][C:8]([CH3:12])([CH3:13])[O:9][C:10]1=[O:11])[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 577069905-(2-Fluoro-3-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178418443HCID 178418443, compound

Product 1

HCID 57705536HCID 57705536, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL round bottom flask was charged with 5-(2-fluoro-3-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 77.B (5.00 g, 17.8 mmol) and THF (100 mL). The resulting slurry was cooled to 0° C., and to it was added ethylmagnesium bromide (available from Aldrich) (3.0 M/ether) (11.9 mL, 35.7 mmol) dropwise over 15 minutes. The cooling bath was removed, and the mixture was stirred for 1 hour at ambient temperature. The reaction was quenched with 1 N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), and concentrated to afford 5-(1-(2-fluoro-3-methoxyphenyl)propyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 77.C (5.17 g, 93.4% yield) as a yellow oil (5.2 g, 93%). The product thus obtained was used without further purification.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched with 1 N HCl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-65afe993183e4acd8c21ffcd29a20c91
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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