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

HRID 1662353Notes

Reaction equation

HRID 1662353 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.[CH2:19]([Mg]Cl)[CH:20]=[CH2:21]>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])[CH2:21][CH:20]=[CH2:19])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6053805-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178418473HCID 178418473, compound

Product 1

HCID 577059815-(1-(3-Hydroxyphenyl)-3-butenyl)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 36.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.1 (8.00 g, 32 mmol) in THF (100 mL) was added allylmagnesium chloride (available from Aldrich) (2.0 M in THF) (97 mL, 193 mmol) dropwise at 0° C. over 1 hour. When the addition was complete, the reaction was quenched with 1 N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), and concentrated. The crude product was chromatographed on silica gel (20-30% EtOAc/hexane) to afford 43.1 (3.4 g, 36%) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-06196cbddf6641f7ac8fd606a4106fea
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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