Dimethylformamide → (S)-5-Oxotetrahydrofuran-2-carbonyl chloride

HRID 60737

Reaction equation

HRID 60737 reaction equation
[O:1]=[C:2]1[O:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.CN(C=O)C.C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl>[O:1]=[C:2]1[O:6][C@H:5]([C:7]([Cl:18])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 636468(2S)-5-oxooxolane-2-carboxylic acid2×

Product 1

HCID 10975648(S)-5-Oxotetrahydrofuran-2-carbonyl chlorideYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-5-oxotetrahydrofuran-2-carboxylic acid (compound 28a, 70 g, 539 mmol) and a drop of DMF in anhydrous DCM (500 mL) was added oxalyl dichloride (137 g, 1.07 mol) dropwise. The reaction mixture was stirred at room temperature for 3 hours. The reaction was then concentrated in vacuo to afford 70 g crude product of (2S)-5-oxotetrahydrofuran-2-carbonyl chloride (compound 28b), which was used in next step without further purification.

Workup

  1. concentrationThe reaction was then concentrated in vacuo

Sources & evidence

ORD record
ord-77eed8f0a2d446d19676e36e967d82c0
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Linked notes

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