Methyl iodide → Methyl 2-(3-benzoylphenyl)propanoate

HRID 1731180Notes

Reaction equation

HRID 1731180 reaction equation
[CH2:1]([Li])CCC.C(NCC)C.[C:11]([C:19]1[CH:20]=[C:21]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:22]=[CH:23][CH:24]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CI>CCCCCC.O1CCCC1>[C:11]([C:19]1[CH:20]=[C:21]([CH:25]([CH3:1])[C:26]([O:28][CH3:29])=[O:27])[CH:22]=[CH:23][CH:24]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8021DiethylamineHCID 10634678Desmethyl Ketoprofen Methyl EsterHCID 178418339Butyllithium

Product 1

HCID 529083Methyl 2-(3-benzoylphenyl)propanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

138 ml of a solution of 1.55N butyl lithium in hexane was introduced over 20 minutes at -40° C to a mixture of 775 ml of tetrahydrofuran, 775 ml of hexamethyl phosphor-triamide and 21.5 ml of diethylamine and after stirring for 20 minutes, a solution of 52.5 g of the above ester in 470 ml of tetrahydrofuran was added over 20 minutes. Then, 38 ml of methyl iodide were added thereto and the mixture was stirred for 30 minutes at about -40° C and then was progressively returned to 20° C. The reaction mixture was poured into 3 liters of water-ice mixture and was stirred and extracted with isopropyl ether. The extracts were washed with water and evaporated to dryness under reduced pressure to obtain methyl 2-(m-benzoyl-phenyl)-propionate which was used as is for the saponification.

Workup

  1. stirringthe mixture was stirred for 30 minutes at about -40° C
  2. customwas progressively returned to 20° C
  3. stirringwas stirred
  4. extractionextracted with isopropyl ether
  5. washThe extracts were washed with water
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6d69083b4a7144b89976f5c0c5ebfb4a
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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