Acetic Anhydride → HCID 53234607, compound

HRID 239630Notes

Reaction equation

HRID 239630 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:18](OC(=O)C)(=O)[CH3:19].C([O-])(=O)C.[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:10])[C:11]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:17][C:18]=2[CH3:19])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 60209054HCID 60209054, compound

Product 1

HCID 53234607HCID 53234607, compoundYield 68%

Procedure

Intermediate 65 (1.50 g, 6.51 mmoles) was taken in a RB flask and to this acetic anhydride (15 ml) and sodium acetate (3.74 g, 45.60 mmoles) were added and the mixture was refluxed for 12 h. After cooling to RT, the reaction mixture was quenched by the addition of ice cold water. The solid formed was filtered and washed with water. The product was dried under vacuum to afford the title compound as colourless solid (1.1 g, 68% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.05(dd, J=7.9,1.6 Hz, 1H), 7.83(m,1H), 7.66(d, J=8.1 Hz, 1H), 7.50(m, 2H), 7.24-7.13(m, 3H), 2.29(s, 3H).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 12 h
  3. customthe reaction mixture was quenched by the addition of ice cold water
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-23373a58259d4cca939880a2802816ac
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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