Ethyl Acetate → HCID 76529970, compound

HRID 1765701Notes

Reaction equation

HRID 1765701 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([Cl:14])P(CCC)(CCC)=O)[CH3:2].C([Li])CCC.[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>[CH2:1]([O:3][C:4](=[O:15])[C:5]([Cl:14])=[CH:26][C:25]1[CH:28]=[CH:29][C:22]([I:21])=[CH:23][CH:24]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 966574-IodobenzaldehydeHCID 57424207HCID 57424207, compoundHCID 178418339Butyllithium

Product 1

HCID 76529970HCID 76529970, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A stirred, cooled (−78° C.) solution of chloro-(dipropyl-phosphinoyl)-acetic acid ethyl ester (6.1 g, 23.5 mmol) in anhydrous tetrahydrofuran (700 mL) was treated with a 1.6M solution of n-butyl lithium in hexanes (14 mL, 22 mmol). After 10 min, the reaction mixture was cannulated into a cooled (−78° C.) solution of 4-iodo-benzaldehyde (2.61 g, 11.2 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 4–5% ethyl acetate in hexane as the eluent to afford the title compound as a 1:1 mixture of E and Z isomers (3.6 g, 95%).

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-f94d2498c60f4cf0b326633a118957c6
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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