Methyl 4-Formylbenzoate → methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)benzoate

HRID 909048Notes

Reaction equation

HRID 909048 reaction equation
[CH3:1][C:2]([O:5][C:6]([CH2:8]P(OC)(OC)=O)=[O:7])([CH3:4])[CH3:3].[H-].[Na+].[CH:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=O>C1COCC1>[CH3:26][O:25][C:23](=[O:24])[C:22]1[CH:27]=[CH:28][C:19](/[CH:17]=[CH:8]/[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 24758Sodium hydrideHCID 4564495tert-Butyl Dimethylphosphonoacetate

Product 1

HCID 42640359methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)benzoateYield 118.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl P,P-dimethylphosphonoacetate (Fluka, 1.43 g, 6.4 mmol) in THF (40 mL) was added NaH (Alderich, 60%, 536 mg, 13.4 mmol) portionwise at rt over 30 min. Methyl 4-formylbenzoate (Alderich, 1.0 g, 6.09 mmol) was then added and the reaction mixture was stirred at rt for 4 hrs. The reaction was quenched with water and extracted with EtOAc. The organic layer was separated, and dried over Na2SO4. The mixture was then concentrated to give the crude 4-((E)-2-tert-butoxycarbonyl-vinyl)-benzoic acid methyl ester (1.89 g, 118%).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-09c271f329b44f38b9aa45aa3dea52b2
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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