Diethyl Oxalate → HCID 18651189, compound

HRID 1590403Notes

Reaction equation

HRID 1590403 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:9])[CH2:7][F:8])[CH3:4].[C:10](OCC)(=O)[C:11](OCC)=O.[Cl:20][C:21]1[CH:22]=[C:23]([C@@H:28]2[CH2:30][C@H:29]2[CH:31]=O)[CH:24]=[CH:25][C:26]=1[Cl:27]>O.C1COCC1>[CH2:3]([O:5][C:6](=[O:9])/[C:7](/[F:8])=[C:31](/[C@@H:29]1[CH2:30][C@H:28]1[C:23]1[CH:24]=[CH:25][C:26]([Cl:27])=[C:21]([Cl:20])[CH:22]=1)\[CH2:10][CH3:11])[CH3:4]

Participants

7

Reactant 4

HCID 7268Diethyl OxalateHCID 9988Ethyl fluoroacetateHCID 24758Sodium hydrideHCID 18651195HCID 18651195, compound

Product 1

HCID 18651189HCID 18651189, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.74 g of a 60% dispersion in mineral oil) (ex BDH)in THF (30 ml) was treated with Ethylfluoroacetate (2.7 ml) (ex Lancaster) and diethyl oxalate (ex BDH) (3.8 ml). After 4 hours at 80° C., (±)-trans-2-(3,4-dichlorophenyl)cyclopropylmethanal (6 g) (example 2(i) and example 1(ii) to (iv)) was added. After 18 hours at 25°, water was added and the mixture worked up in the usual manner. Purification by chromotography (silica, hexane/ether) gave (±)-Ethyl-(2Z)-3-[trans-2-(3,4-dichlorophenyl)cyclopropyl]-2-fluoropent-2-enoate (4 g). NMR 1H 7.30(1H,d), 7.15(1H,d), 6.90(1H,dd), 5.70(1H,dd), 4.30(2H,q), 2.08(2H,m), 1.35(2H,m), 1.30(3H,t).

Workup

  1. waitAfter 18 hours at 25°
  2. customPurification by chromotography (silica, hexane/ether)

Sources & evidence

ORD record
ord-6a058dd2db4543d28345e84faa8ad3d3
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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