Oxalyl chloride → (S)-2-(4-fluorophenyl)pent-4-enoyl chloride

HRID 749456Notes

Reaction equation

HRID 749456 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:12][CH:13]=[CH2:14])[C:9](O)=[O:10])=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:12][CH:13]=[CH2:14])[C:9]([Cl:18])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 15536021(2S)-2-(4-fluorophenyl)pent-4-enoic acid

Product 1

HCID 15536025(S)-2-(4-fluorophenyl)pent-4-enoyl chlorideYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

(2S)-2-(4-Fluorophenyl)pent-4-enoic acid (see Tetrahedron Letters; 2002; 6617-6620; 1.2 g, 6.0 mmol) was dissolved in CH2Cl2 (15 mL) and to the resultant solution was added oxalyl chloride (1.1 g, 9.0 mmol) followed by one drop of DMF. The mixture was stirred for 2 h at room temperature. The solvent was removed by evaporation and there was obtained 1.2 g (98%) of (2S)-2-(4-fluorophenyl)pent-4-enoyl chloride as an oil. 1H NMR (300 MHz, CDCl3): 2.6 (q, 1H), 2.9 (q, 1H), 4.1 (t, 1H), 5.0-5.2 (m, 2H), 5.6-5.8 (m, 1H), 7.1 (t, 2H), 7.3 (m, 2H).

Workup

  1. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-34aef157f4b7413da6710b9ec860c9d1
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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