Aluminium lithium hydride → 4H-Thieno[2,3-d]azepin-4-ol, 5,6,7,8-tetrahydro-

HRID 1511612Notes

Reaction equation

HRID 1511612 reaction equation
FC(F)(F)S([N:6]1[CH2:12][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][S:16][C:9]=2[CH2:8][CH2:7]1)(=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[S:16]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:12][CH:11]([OH:13])[C:10]=2[CH:14]=[CH:15]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 68409707HCID 68409707, compound

Product 1

HCID 116368784H-Thieno[2,3-d]azepin-4-ol, 5,6,7,8-tetrahydro-Yield 48.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.5 g of 6-trifluoromethanesulfonyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepin-4-one prepared in the step 4 in 30 mL of dry THF was slowly dropped into an ice-cooled solution of 0.63 g of lithium aluminum hydride in 20 mL of dry THF. The reaction solution was gradually heated followed by heating to reflux overnight. Then the reaction solution was cooled, ice was gradually added thereto so that an excess 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 0.69 g of the objective compound.

Workup

  1. temperatureThe reaction solution was gradually heated
  2. temperatureby heating
  3. temperatureto reflux overnight
  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-cc238c24a5ef4b83b24d1bc67d281a35
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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