Acetic Anhydride → HCID 118277016, compound

HRID 1053698Notes

Reaction equation

HRID 1053698 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH:8]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][C:10](O)=[O:11])[CH:7]=1.C(OC(=O)C)(=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH:8]2[CH2:13][C:14](=[O:16])[O:15][C:10](=[O:11])[CH2:9]2)[CH:7]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 118276985HCID 118276985, compound

Product 1

HCID 118277016HCID 118277016, compound

Conditions

Temperature
130 °C

Procedure

Asymmetry, 2001, 12, 419-426), 4-(5-chloro-2-nitro-phenyl)tetrahydropyran-2,6-dione (18c) is prepared by heating 3-(5-chloro-2-nitro-phenyl)pentanedioic acid (18b) (2.88 g, 10.0 mmol) in acetic anhydride (Ac2O) (2.83 mL, 3.06 g, 30 mmol) at reflux (about 130° C. oil bath temperature). After cooling to room temperature, the title compound (18c) is precipitated with diethyl ether (Et2O) the solid collected by filtration, washed with cold Et2Oand dried under reduced pressure to remove residual solvents.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe title compound (18c) is precipitated with diethyl ether (Et2O) the solid
  3. filtrationcollected by filtration
  4. washwashed with cold Et2Oand
  5. customdried under reduced pressure
  6. customto remove residual solvents

Sources & evidence

ORD record
ord-e46037c7755e49a18918db1dc2ddcd49
Source dataset
uspto-grants-2016_07
Patent number
US09394236B2

Reaction notes

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