Ethyl Acetate → HCID 76529970, compound

HRID 1869828Notes

Reaction equation

HRID 1869828 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 (70 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-759972f87903454ba192d1fe5d359810
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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