Water → HCID 68523939, compound

HRID 2247667Notes

Reaction equation

HRID 2247667 reaction equation
C([O:4][CH:5]1[C:10]2[CH:11]=[CH:12][S:13][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=O)C.[Br:14]N1C(=O)CCC1=O.O.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:14][C:12]1[S:13][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([OH:4])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 68521941HCID 68521941, compound

Product 1

HCID 68523939HCID 68523939, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4,5,6,7-tetrahydro-1-benzothien-4-yl acetate (5.1 g, 26 mmol) in chloroform (30 ml) was added N-bromosuccinimide (5 g, 28 mmol) at 0° C. with stirring, and the resulting mixture was stirred at room temperature for 3 hours. After stirring, the reaction mixture was poured into water (40 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo. Subsequently, to a solution of the residue thus obtained in a mixed solvent of tetrahydrofuran (20 ml) and water (20 ml) was added sodium hydroxide (2.3 g, 57 mmol) with stirring, and the resulting mixture was stirred for 2 hours. After stirring, the reaction mixture was poured into water (50 ml) to quench the reaction and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:7) as the eluent to afford the title compound (5.0 g) in a yield of 82% as a colourless oily product.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. stirringAfter stirring
  3. extractionextracted with ether
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe filtrate was evaporated in vacuo
  8. customSubsequently, to a solution of the residue thus obtained in a mixed solvent of tetrahydrofuran (20 ml) and water (20 ml)
  9. stirringwith stirring
  10. stirringthe resulting mixture was stirred for 2 hours
  11. stirringAfter stirring
  12. customto quench
  13. customthe reaction
  14. extractionextracted with ether
  15. washThe extract was washed with a saturated aqueous solution of sodium chloride
  16. dry with materialdried over magnesium sulfate
  17. filtrationAfter filtration
  18. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-5789fb05c91c4efba76d900398bb2533
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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