Ethyl Acetate → (E)-3-(4-Iodo-phenyl)-2-methyl-acrylic acid ethyl ester

HRID 1765700Notes

Reaction equation

HRID 1765700 reaction equation
C([C:3](CC)(CC)[CH:4](P(O)(O)=O)[C:5]([O-:7])=[O:6])C.[CH2:16]([Li])[CH2:17]CC.[I:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C(OCC)(=O)C>O1CCCC1.CCCCCC>[CH2:16]([O:7][C:5](=[O:6])/[C:4](/[CH3:3])=[CH:26]/[C:25]1[CH:28]=[CH:29][C:22]([I:21])=[CH:23][CH:24]=1)[CH3:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 966574-IodobenzaldehydeHCID 92003523Triethyl-2-phosphonopropionateHCID 178418339Butyllithium

Product 1

HCID 57424206(E)-3-(4-Iodo-phenyl)-2-methyl-acrylic acid ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A stirred, cooled (−78° C.) solution of triethyl-2-phosphonopropionate (10 g, 41.9 mmol) in anhydrous tetrahydrofuran (100 mL) was treated with a 1.6M solution of n-butyl lithium in hexanes (25 mL, 40 mmol). After 10 min, the reaction mixture was cannulated into a cooled (−78° C.) solution of 4-iodo-benzaldehyde (4.66 g, 20 mmol) in tetrahydrofuran (25 mL). After 30 minutes, it was quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford an oil that was subjected to flash column chromatography over silica gel (230–400 mesh) using 9–10% ethyl acetate in hexane as the eluent to afford the title compound (6.3 g, 99%).

Workup

  1. waitAfter 30 minutes
  2. customit was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford an oil that

Sources & evidence

ORD record
ord-593d708ceb45495cbc3fefd14ff79672
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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