Tetrahydrofuran → HCID 86742372, compound

HRID 35367Notes

Reaction equation

HRID 35367 reaction equation
[O:1]1[CH2:6][C:5](=O)[NH:4][C@@H:3]2[CH2:8][CH2:9][O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C@H:2]12.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-:23].[Na+].[O:25]1CCCC1>>[C:2]([OH:1])(=[O:25])/[CH:3]=[CH:8]\[C:9]([OH:10])=[O:23].[O:1]1[CH2:6][CH2:5][NH:4][C@@H:3]2[CH2:8][CH2:9][O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C@H:2]12

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86742374HCID 86742374, compound

Product 1

HCID 86742372HCID 86742372, compound

Procedure

Cis-4a,5,6,11b-tetrahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine-3(4H)-one (0.01M) was added via a solution funnel to a suspension of 0.005M lithium aluminum hydride in 100 ml of dry tetrahydrofuran. The mixture was refluxed for five hours, cooled in ice and decomposed with 15% NaOH. After stirring overnight the mixture was filtered and the solvent removed from the filtrate. The residue was dissolved in ether and treated with a solution of maleic acid in ether to give the title compound. An analytical sample was recrystallized from ethyl acetate, mp. 197°-198° C. (dec.).

Workup

  1. temperatureThe mixture was refluxed for five hours
  2. temperaturecooled in ice
  3. filtrationwas filtered
  4. customthe solvent removed from the filtrate
  5. dissolutionThe residue was dissolved in ether
  6. additiontreated with a solution of maleic acid in ether

Sources & evidence

ORD record
ord-4f32ed28aa7742aebdb6e30d41d2ceec
Source dataset
uspto-grants-1988_08
Patent number
US04766212

Reaction notes

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