Acetic Anhydride → HCID 131728925, compound

HRID 551702Notes

Reaction equation

HRID 551702 reaction equation
C([O-])(=O)C.[K+].[CH2:6]([C:8]([CH2:13][CH2:14][CH:15]=[CH2:16])=[CH:9][C:10](O)=O)[CH3:7].C(OC(=O)C)(=O)C.COP([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])(OC)=O.[Cl-].[Li+].N12CCCN=C1CCCCC2>O.C(#N)C.CC(N(C)C)=O>[CH2:6]([C:8]1[C@H:13]2[C@H:16]([CH2:15][C:14]2=[CH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:10][CH:9]=1)[CH3:7]

Participants

10

Reactant 6

HCID 7918Acetic AnhydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 4564495tert-Butyl DimethylphosphonoacetateHCID 86646159HCID 86646159, compound

Product 1

HCID 131728925HCID 131728925, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

Potassium acetate (2.56 g, 26.1 mmol) was added to a dimethylacetamide (25 mL) solution of 3-ethylhepta-2,6-dienoic acid (2.01 g, 13.0 mmol) and acetic anhydride (2.66 g, 26.1 mmol), and the mixture was stirred at room temperature for 1 hour and then stirred at 120° C. for 3 hours. The mixture was treated with an ice water solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was applied to column chromatography to obtain a pale yellow oil substance. The substance obtained here was added to an acetonitrile (40 mL) solution of tert-butyl dimethylphosphonoacetate (2.60 g, 16.6 mmol), lithium chloride (0.70 g, 16.6 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.60 g, 16.6 mmol) stirred in advance for 1 hour, and the mixture was further stirred for 3.5 hours. The mixture was treated with water, and volatile portions were then distilled off under reduced pressure, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a yellow oil substance (2.20 g, 68%).

Workup

  1. stirringstirred at 120° C. for 3 hours
  2. extractionfollowed by extraction with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customto obtain a pale yellow oil substance
  6. customThe substance obtained here
  7. stirringstirred in advance for 1 hour
  8. stirringthe mixture was further stirred for 3.5 hours
  9. distillationwere then distilled off under reduced pressure
  10. extractionfollowed by extraction with ethyl acetate
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. distillationThe solvent was distilled off under reduced pressure
  13. customthe residue was purified by silica gel column chromatography
  14. customto obtain the compound of interest as a yellow oil substance (2.20 g, 68%)

Sources & evidence

ORD record
ord-e992c2f1c1e441b3992129c41518c1cd
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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