Oxalyl chloride → 3-(2-(2-(2-(1,3-Dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoyl chloride

HRID 45729Notes

Reaction equation

HRID 45729 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]([OH:25])=O.C(Cl)(=O)C([Cl:29])=O>C(Cl)Cl.CN(C=O)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]([Cl:29])=[O:25]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 144623883-(2-(2-(2-(1,3-Dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoic acid

Product 1

HCID 866723473-(2-(2-(2-(1,3-Dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoic acid (700 mg, 1.99 mmol, 1.00 equiv) in anhydrous DCM (30.0 mL), then oxalyl dichloride (0.7 mL) was added dropwise at room temperature. Two drops of anhydrous DMF were then added. The resulting solution was heated to reflux for 40 min. The solvent was removed under vacuum to yield 750 mg of 3-(2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)ethoxy)ethoxy)propanoyl chloride as pale yellow oil, which was used directly for the next reaction step without further purification.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 40 min
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-9e4cccf24b6b4980b14ac92df2305b3c
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

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