Diethyl Oxalate → Ethyl 3-(3,4-dichlorophenyl)-2-fluoroprop-2-enoate

HRID 1728311Notes

Reaction equation

HRID 1728311 reaction equation
[H-].[Na+].C(OCC)(=O)C(OCC)=O.[F:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH:24]=O>C1COCC1>[Cl:20][C:21]1[CH:22]=[C:23]([CH:24]=[C:14]([F:13])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:26]=[CH:27][C:28]=1[Cl:29]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 9988Ethyl fluoroacetateHCID 227103,4-DichlorobenzaldehydeHCID 24758Sodium hydride

Product 1

HCID 54301345Ethyl 3-(3,4-dichlorophenyl)-2-fluoroprop-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of sodium hydride (0.33 g), diethyl oxalate (1.83 g), ethyl fluoroacetate (1.33 g) and anhydrous THF (10 ml) was heated under reflux for 4 hours whereupon 3,4-dichlorobenzaldehyde (2.18 g) (ex.Aldrich) in THF was added. After 18 hours at room temperature the reaction mixture was partitioned between water and ether and worked up in conventional fashion. Purification by chromatography (silica, 80:20 hexane/ether) gave (Z) ethyl 3-(3,4-dichlorophenyl)-2-fluoroprop-2-enoate (2.1 g.

Workup

  1. temperaturewas heated
  2. additionwas added
  3. customAfter 18 hours at room temperature the reaction mixture was partitioned between water and ether
  4. customPurification by chromatography (silica, 80:20 hexane/ether)

Sources & evidence

ORD record
ord-25d5ad82c10f4d05949740f838e8f5a4
Source dataset
uspto-grants-1994_07
Patent number
US05326755

Reaction notes

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