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

HRID 2101780Notes

Reaction equation

HRID 2101780 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[C:7]2[C:12](=[O:13])[O:11][C:10]([CH3:15])([CH3:14])[O:9][C:8]2=[O:16])=[CH:4][CH:3]=1.[CH:19]1([Mg]Cl)[CH2:21][CH2:20]1>C1COCC1>[CH:19]1([CH:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:18][CH:17]=2)[CH:7]2[C:8](=[O:16])[O:9][C:10]([CH3:15])([CH3:14])[O:11][C:12]2=[O:13])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 3705415-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178478986HCID 178478986, compound

Product 1

HCID 576724845-(Cyclopropyl(4-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 21.1 (8.00 g, 32 mmol) in THF (100 mL) was added a 2.0 M solution of cyclopropylmagnesium chloride in THF (97 mL, 193 mmol (commercially available from Aldrich)) dropwise at 0° C. over 1 hour. Upon completion of the addition, the mixture was quenched with 1 N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was chromatographed on silica gel (20-30% EtOAc/hexane) to afford 21.2.

Workup

  1. additionUpon completion of the addition
  2. customthe mixture was quenched with 1 N HCl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed on silica gel (20-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-0e0ade49e38b4316be99e5bfa91d5f79
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

Loading…