5-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 5-(1-(3-Hydroxyphenyl)-2-propenyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1662334Notes

Reaction equation

HRID 1662334 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[C:14](=[O:15])[O:13][C:12]([CH3:17])([CH3:16])[O:11][C:10]2=[O:18])[CH:5]=[CH:6][CH:7]=1.[CH:19]([Mg]Br)=[CH2:20]>C1COCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH:9]2[C:10](=[O:18])[O:11][C:12]([CH3:16])([CH3:17])[O:13][C:14]2=[O:15])[CH:19]=[CH2:20])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6053805-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178418507HCID 178418507, compound

Product 1

HCID 577056725-(1-(3-Hydroxyphenyl)-2-propenyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.1 (6.0 g, 24.17 mmol) in THF, was added vinylmagnesium bromide (available from Aldrich) (207.2 mL, 145.0 mmol) via cannula at 0° C. The resulting heterogeneous mixture was warmed to room temperature, stirred for 30 minutes, and quenched with 1 N aq. HCl. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to provide 15.1 as a yellow oil which was used in the next step without further purification.

Workup

  1. customquenched with 1 N aq. HCl
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5bba2e28fc5e4c5698ac54d2e233e403
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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