Tetrahydrofuran → HCID 22888181, compound

HRID 992452Notes

Reaction equation

HRID 992452 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=[O:3].[Cl:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1.[Mg].O1CCCC1>C(OCC)C>[CH2:7]([O:6][C:1](=[O:5])[C:2]([C:13]1[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=1)([OH:3])[CH3:4])[CH3:8]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 12041Ethyl pyruvateHCID 125101-Chloro-4-iodobenzeneHCID 5462224Magnesium

Product 1

HCID 22888181HCID 22888181, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 11.5 g ethyl pyruvate in 20 ml diethylether is slowly added under cooling (0° C.), a freshly prepared Grignard solution (from 23.9 g 4-chloro-iodobenzene and 3 g magnesium turnings). Some tetrahydrofurane is added to prevent the formation of viscous suspension. After stirring for 2 hours at room temperature the reaction is quenched by pouring it onto a mixture of ice and 2N sulfuric acid. Extraction of the suspension with diethyl ether followed by washing with brine, drying over sodium sulfate and evaporation leads to a residue which is purified on silicagel (hexane-ethyl acetate) to obtain 2-(4-chlorophenyl)-2-hydroxy propionic acid ethyl ester as yellowish oil.

Workup

  1. customis quenched
  2. additionby pouring it
  3. additiononto a mixture of ice and 2N sulfuric acid
  4. extractionExtraction of the suspension with diethyl ether
  5. washby washing with brine
  6. dry with materialdrying over sodium sulfate and evaporation
  7. customis purified on silicagel (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4ffac6cf121549109aa9216d2c46159b
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

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