Benzaldehyde → Methyl cinnamate, (Z)-

HRID 2376678Notes

Reaction equation

HRID 2376678 reaction equation
C1OCCOCCOCCOCCOCCOC1.FC(F)(F)COP([CH2:31][C:32]([O:34][CH3:35])=[O:33])(OCC(F)(F)F)=O.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:48](=O)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>O1CCCC1.C1(C)C=CC=CC=1>[C:49]1(/[CH:48]=[CH:31]\[C:32]([O:34][CH3:35])=[O:33])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 2855718-Crown-6HCID 184894Nsc 634137HCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 6428458Methyl cinnamate, (Z)-

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

9.4 g of 18-crown-6 and 1.7 ml of methyl [bis(2,2,2-trifluoroethoxy)-phosphoryl]acetate are dissolved under argon in 120 ml of dry tetrahydro-furan and cooled to −78° C. 14.3 ml of a 0.5 molar solution of potassium bis(trimethylsilyl)amide in toluene are added to this mixture, followed by 0.85 ml of benzaldehyde. After stirring at −78° C. for thirty minutes, the reaction mixture is quenched by adding saturated ammonium chloride solution and extracted with five portions each of 50 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and then the solvent is removed in vacuo. The residue is purified on silica gel with n-heptane:ethyl acetate=20:1 as eluent. 1.1 g of methyl (Z)-3-phenylacrylate are obtained as an oil.

Workup

  1. customthe reaction mixture is quenched
  2. additionby adding saturated ammonium chloride solution
  3. extractionextracted with five portions each of 50 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. customthe solvent is removed in vacuo
  6. customThe residue is purified on silica gel with n-heptane

Sources & evidence

ORD record
ord-71c0f3d7f0104ac5b1c8af5c93bfc3af
Source dataset
uspto-grants-2008_12
Patent number
US07468369B2

Reaction notes

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