Ethyl Acetate → 2-Propenoic acid, 3-(4-iodophenyl)-, ethyl ester

HRID 1765695Notes

Reaction equation

HRID 1765695 reaction equation
C([Li])CCC.[I:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16]>O1CCCC1.CCCCCC>[CH2:19]([O:18][C:15](=[O:17])[CH:16]=[CH:11][C:10]1[CH:13]=[CH:14][C:7]([I:6])=[CH:8][CH:9]=1)[CH3:20]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 966574-IodobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 541932622-Propenoic acid, 3-(4-iodophenyl)-, ethyl esterYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred, cooled (−78° C.) solution of triethylphosphonoacetate (11.1 mL, 56 mmol) in anhydrous tetrahydrofuran (100 mL) was treated with a 1.6M solution of n-butyl lithium in hexanes (27 mL, 43.75 mmol). After 10 min, the reaction mixture was cannulated into a cooled (−78° C.) solution of 4-iodo-benzaldehyde (6.5 g, 28 mmol) in tetrahydrofuran (20 mL). The reaction mixture was allowed to warm to 0° C. over 1 h. 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 6–8% ethyl acetate in hexane as the eluent to afford the title compound (2.7 g pure, 3.2 g˜95% pure, 69%).

Workup

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

Sources & evidence

ORD record
ord-1e3653e9259a411f956ae3d2ebd3217c
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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