Diethyl Oxalate → Ethyl (3-benzyloxy-6-trifluoromethyl-2-nitrophenyl)pyruvate

HRID 1067788Notes

Reaction equation

HRID 1067788 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:20]([O-:22])=[O:21])=[C:11]([CH3:19])[C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](OCC)(=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].[O-]CC.[K+]>C(OCC)C>[CH2:1]([O:8][C:9]1[C:10]([N+:20]([O-:22])=[O:21])=[C:11]([CH2:19][C:23](=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 105430343-Benzyloxy-6-trifluoromethyl-2-nitrotolueneHCID 23670592Potassium ethoxide

Product 1

HCID 54393638Ethyl (3-benzyloxy-6-trifluoromethyl-2-nitrophenyl)pyruvate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The reaction was carried out in a manner similar to Reference Example 12 b) except for using 14.6 g (46.9 mmol) of 3-benzyloxy-6-trifluoromethyl-2-nitrotoluene, 13.7 g (93.8 mmol) of diethyl oxalate, 7.90 g (93.8 mmol) of potassium ethoxide and 300 ml of diethyl ether. Ethyl (3-benzyloxy-6-trifluoromethyl-2-nitrophenyl)pyruvate was thus obtained in the yield of 10.9 g (56.9%).

Sources & evidence

ORD record
ord-5da1cd5b67554b918c65941775f0cdf9
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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