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

HRID 2377307Notes

Reaction equation

HRID 2377307 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-3f3aa6f2138b4cada1eccc7635fd0632
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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