5-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 5-[Cyclopropyl(3-hydroxyphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1662369Notes

Reaction equation

HRID 1662369 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH:5]=[C:6]1[C:11](=[O:12])[O:10][C:9]([CH3:14])([CH3:13])[O:8][C:7]1=[O:15].[CH:19]1([Mg]Br)[CH2:21][CH2:20]1>C1COCC1>[CH:19]1([CH:5]([C:4]2[CH:16]=[CH:17][CH:18]=[C:2]([OH:1])[CH:3]=2)[CH:6]2[C:7](=[O:15])[O:8][C:9]([CH3:14])([CH3:13])[O:10][C:11]2=[O:12])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 6053805-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178418630HCID 178418630, compound

Product 1

HCID 577059545-[Cyclopropyl(3-hydroxyphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 66.6S (2.00 g, 8.06 mmol) in THF (25 mL) was added cyclopropylmagnesium bromide (available from Aldrich) (0.5M, 96.7 mL, 48.3 mmol) via cannula at 0° C. The resulting heterogeneous mixture was warmed to room temperature, stirred for 30 minutes, and quenched with 1 N aqueous HCl. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel flash chromatography (10-35% EtOAc/hexane) to afford 5-(cyclopropyl(3-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 66.6T (2.04 g, 87% yield) as a yellow oil.

Workup

  1. customquenched with 1 N aqueous HCl
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel flash chromatography (10-35% EtOAc/hexane)

Sources & evidence

ORD record
ord-28ace2ea874842ca8c3605167e8eb7a6
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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