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 1662326Notes

Reaction equation

HRID 1662326 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]1([Mg]Br)[CH2:21][CH2:20]1>C1COCC1>[CH:19]1([CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=2)[CH:9]2[C:10](=[O:18])[O:11][C:12]([CH3:16])([CH3:17])[O:13][C:14]2=[O:15])[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 8.1 (2.0 g, 8.06 mmol) in THF, was added cyclopropylmagnesium bromide (available from Aldrich) (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 aq. HCl. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel flash chromatography (10-35% EtOAc/hexane) to afford 8.2 (2.04 g, 87.2% yield) as a yellow oil.

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, dried sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (10-35% EtOAc/hexane)

Sources & evidence

ORD record
ord-f4604257cb81405fb506e8952cd7d971
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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