Ethyl formate → Ethyl 3-oxo-2-(3-chloro-5-methylphenyl)propionate

HRID 1760024Notes

Reaction equation

HRID 1760024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH:15](OCC)=[O:16]>C(OCC)C>[O:16]=[CH:15][CH:9]([C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 22600092Ethyl 3-chloro-5-methylphenylacetate

Product 1

HCID 22600090Ethyl 3-oxo-2-(3-chloro-5-methylphenyl)propionateYield 61.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared analogously to the method described in Example N(v) above from ethyl 3-chloro-5-methylphenylacetate (4.89 g; 23 mmol; from step (iv) above), ethyl formate (3.3 g; 41.4 mmol) and Na (0.63 g; 27.6 mmol; added in small lumps) in dry ethyl ether (50 mL) to yield 3.4 g (61%) of the sub-title compound as a clear oil which slowly crystallised on standing.

Workup

  1. customPrepared analogously to the method

Sources & evidence

ORD record
ord-a187f5d7eec14e35b50e8a61f56eeab3
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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