Oxalyl chloride → (S)-2-phenylpent-4-enoyl chloride

HRID 429483Notes

Reaction equation

HRID 429483 reaction equation
[C:1]1([C@H:7]([CH2:11][CH:12]=[CH2:13])[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:17])=O>CN(C)C=O.ClCCl>[C:1]1([C@H:7]([CH2:11][CH:12]=[CH2:13])[C:8]([Cl:17])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 12086387(S)-2-phenylpent-4-enoic acid

Product 1

HCID 12086388(S)-2-phenylpent-4-enoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine (S)-2-phenylpent-4-enoic acid (1.53 g, 8.7 mmol), dichloromethane (10 mL), and dimethylformamide (1 drop). Add oxalyl chloride (1 mL, 11.46 mmol). After 2 hours, evaporate in vacuo to give (S)-2-phenylpent-4-enoyl chloride. Combine with toluene (10 mL) and add, with vigorous stirring, to a cooled (ice bath) aqueous solution of methylamine (2 mL, 40%). After 1 hour, partition the reaction mixture between water and dichloromethane. Separate the layers, dry the organic over MgSO4, filter, and evaporate in vacuo to give a residue. Triturate the residue with hexane to give a solid. Collect the solid by filtration and dry to give (S)-2-phenylpent-4-enoic acid, N-methyl amide: mp; 97-99° C. Rf=0.53 (silica gel, 50% ethyl acetate/hexane).

Workup

  1. customevaporate in vacuo

Sources & evidence

ORD record
ord-daa27d91e5e04a359f42ae4b2d43834a
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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