Dimethylformamide → HCID 17862486, compound

HRID 1766949Notes

Reaction equation

HRID 1766949 reaction equation
[CH2:1]([O:4][C:5]([O:7][CH2:8][C:9]([OH:11])=O)=[O:6])[CH:2]=[CH2:3].C(Cl)(=O)C([Cl:15])=O.CN(C)C=O>O1CCCC1>[CH2:1]([O:4][C:5]([O:7][CH2:8][C:9]([Cl:15])=[O:11])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 17862629HCID 17862629, compound

Product 1

HCID 17862486HCID 17862486, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(allyloxycarbonyloxy)acetic acid (3.03 g, 18.9 mmol) obtained from Example 39-(3) in tetrahydrofuran (30 ml) was cooled to 0° C., and to the solution were added oxalyl chloride (2.64 g, 20.8 mmol) and N,N-dimethylformamide (30 μl). The mixture was warmed to room temperature. After the mixture was stirred for 30 minutes, the solvent was distilled off under reduced pressure, and the resulting residue was purified using simple distillation under reduced pressure to give the title compound (3.04 g, yield 90%) as a colorless oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customthe resulting residue was purified
  3. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-c08b34db2c6b4b17806bdf517091953a
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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