Acetyl chloride → Cis-4-Ethyl-3,4,4a,5,6,11b-Hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine

HRID 35368Notes

Reaction equation

HRID 35368 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C@@H:3]2[CH2:7][CH2:8][O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C@H:2]12.[CH2:16](N(CC)CC)[CH3:17].C(Cl)(=O)C>C(Cl)Cl>[CH2:16]([N:4]1[CH2:5][CH2:6][O:1][C@H:2]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8][CH2:7][C@@H:3]12)[CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86742373cis-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine

Product 1

HCID 86742375Cis-4-Ethyl-3,4,4a,5,6,11b-Hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.01M of cis-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine and 0.011M of triethylamine in 25 ml of methylene chloride was cooled in ice and treated dropwise with 0.01M of acetyl chloride in 10 ml of methylene chloride. After stirring at room temperature overnight, the solution was extracted with dilute hydrochloric acid and dried over magnesium sulfate. Evaporation of the solvent left an oil which was dissolved in 10 ml of dry tetrahydrofuran and this solution added dropwise to a suspension of 0.01M of lithium aluminum hydride in 25 ml of tetrahydrofuran. After refluxing five hours, the mixture was cooled in ice and decomposed with 15% sodium hydroxide. After stirring overnight, the solids were filtered and the solvent removed from the filtrate. Kugelrohr distillation of the residue at 110°-116° C./0.2 mm gave the title compound as an oil.

Workup

  1. extractionthe solution was extracted with dilute hydrochloric acid
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. waitleft an oil which
  5. dissolutionwas dissolved in 10 ml of dry tetrahydrofuran
  6. additionthis solution added dropwise to a suspension of 0.01M of lithium aluminum hydride in 25 ml of tetrahydrofuran
  7. temperatureAfter refluxing five hours
  8. temperaturethe mixture was cooled in ice
  9. stirringAfter stirring overnight
  10. filtrationthe solids were filtered
  11. customthe solvent removed from the filtrate
  12. distillationKugelrohr distillation of the residue at 110°-116° C./0.2 mm

Sources & evidence

ORD record
ord-78cfc93fb90a469d833e696e0be8c633
Source dataset
uspto-grants-1988_08
Patent number
US04766212

Reaction notes

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