Aluminium lithium hydride → HCID 68409883, compound

HRID 1511611Notes

Reaction equation

HRID 1511611 reaction equation
C(O[C:4]([N:6]1[CH2:12][C:11](=[O:13])[C:10]2[CH:14]=[C:15]([CH3:17])[O:16][C:9]=2[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:17][C:15]1[O:16][C:9]2[CH2:8][CH2:7][N:6]([CH3:4])[CH2:12][CH:11]([OH:13])[C:10]=2[CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 68410091HCID 68410091, compound

Product 1

HCID 68409883HCID 68409883, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-ethoxycarbonyl-2-methyl-4,5,7,8-tetrahydrofuro[2,3-d]azepin-4-one (27 mg) prepared in the step 6 in 1 mL of dry THF was slowly dropped into an ice-cooled solution of 6.4 mg of lithium aluminum hydride in 1 mL of dry THF. The reaction solution was gradually heated followed by heating to reflux for 2 hours. Then the reaction solution was cooled, ice was gradually added thereto so that an excess amount of lithium aluminum hydride was decomposed and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 17 mg of the objective compound.

Workup

  1. temperatureThe reaction solution was gradually heated
  2. temperatureby heating
  3. temperatureto reflux for 2 hours
  4. temperatureThen the reaction solution was cooled
  5. additionice was gradually added
  6. extractionthe mixture was subjected to extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-06efd9a77c1e427eafac259f34c85c09
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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