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

HRID 1662502Notes

Reaction equation

HRID 1662502 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH2:16][C:15](=[O:20])[O:14]1>O>[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:16]1[C:17](=[O:19])[O:18][C:13]([CH3:21])([CH3:12])[O:14][C:15]1=[O:20]

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 37744632-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 577069905-(2-Fluoro-3-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 58.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 500 mL round bottom flask was charged with 2-fluoro-3-methoxybenzaldehyde 77.A (available from Aldrich) (28.6 g, 186 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (available from Aldrich) (34.8 g, 241 mmol), and water (350 mL). The heterogeneous mixture was stirred for 2 hours at 90° C. (reflux), cooled to room temperature, and filtered. The resulting off-white solid was triturated with ether to afford 5-(2-fluoro-3-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 77.B (30.6 g, 58.8% yield) as a crystalline white powder.

Workup

  1. temperature(reflux)
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. customThe resulting off-white solid was triturated with ether

Sources & evidence

ORD record
ord-93d16f6535784cd0a8b373193b20b2eb
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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