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

HRID 1869822Notes

Reaction equation

HRID 1869822 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 ester

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-4a488125d8c14b5aab516c519e40e9de
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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