Acetic Anhydride → 2-(p-Fluorobenzoyl)-3-methoxy-2-pentenonitrile

HRID 46567Notes

Reaction equation

HRID 46567 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15](OC)(OC)[CH2:16][CH3:17].C(OC(=O)C)(=O)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8](=[C:15]([O:14][CH3:13])[CH2:16][CH3:17])[C:9]#[N:10])=[O:7])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 1411451,1,1-TrimethoxypropaneHCID 2783172p-Fluorobenzoylacetonitrile

Product 1

HCID 538000562-(p-Fluorobenzoyl)-3-methoxy-2-pentenonitrile

Procedure

A solution containing 30 g. of (p-fluorobenzoyl)acetonitrile, 36.4 g. of trimethylorthopropionate and 57 g. of acetic anhydride is heated in an oil bath at 130° for 3 hours. The ethanol and excess acetic anhydride is distilled off and the residue is diluted with chloroform. The chloroform solution is passed quickly through Magnesol® and concentrated, then cooled to produce the title product.

Workup

  1. additionA solution containing 30 g
  2. distillationThe ethanol and excess acetic anhydride is distilled off
  3. additionthe residue is diluted with chloroform
  4. concentrationconcentrated
  5. temperaturecooled

Sources & evidence

ORD record
ord-2829d8a5983b42ecacf78f16a0bc6537
Source dataset
uspto-grants-1979_11
Patent number
US04173650

Reaction notes

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