Ethanol → HCID 22620483, compound

HRID 840986Notes

Reaction equation

HRID 840986 reaction equation
CS[C:3](SC)=[C:4]1[CH2:10][CH2:9][CH:8]([CH2:11][CH3:12])[C:7]2[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=2[C:5]1=O.[BH4-].[Na+].C[OH:23].[CH2:24]([OH:26])C>>[CH2:11]([CH:8]1[C:7]2[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=2[CH:5]=[C:4]([C:3]([O:26][CH3:24])=[O:23])[CH2:10][CH2:9]1)[CH3:12]

Participants

5

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 4311764Sodium borohydrideHCID 22620529HCID 22620529, compound

Product 1

HCID 22620483HCID 22620483, compound

Procedure

6-[Bis(methylthio)methylene]-9-ethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (0.35 g, 1.31 mmol) was dissolved in ethanol (7 ml), followed by adding thereto sodium tetrahydroborate (0.16 g, 4.35 mmol), and the reaction mixture was heated under reflux for 2 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and boron trifluoride diethyl ether complex (0.56 g, 3.95 mmol) was added to the residue, followed by stirring at room temperature for 20 minutes. Then, methanol (5 ml) was added thereto and the resulting mixture was heated under reflux for 3 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography to obtain 0.20 g of methyl 5-ethyl-6,7-dihydro-5H-benzocycloheptene-8-carboxylate.

Workup

  1. additionby adding
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure, and boron trifluoride diethyl ether complex (0.56 g, 3.95 mmol)
  7. additionwas added to the residue
  8. temperaturethe resulting mixture was heated
  9. temperatureunder reflux for 3 hours
  10. extractionextracted with ethyl acetate
  11. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. distillationThe solvent was distilled off under reduced pressure
  14. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-dc0b97c8f97c4bce92f414fe45c251df
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

Loading…