Sodium borohydride → HCID 13952868, compound

HRID 485873Notes

Reaction equation

HRID 485873 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([O:16][CH3:17])=[CH:6][C:7]2[C:11](=[O:12])[CH:10]([CH3:13])[S:9][C:8]=2[C:14]=1[Cl:15]>C(O)C>[Cl:3][C:4]1[C:5]([O:16][CH3:17])=[CH:6][C:7]2[CH:11]([OH:12])[CH:10]([CH3:13])[S:9][C:8]=2[C:14]=1[Cl:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20197895HCID 20197895, compound

Product 1

HCID 13952868HCID 13952868, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (2.5 g) is added, in small portions, to a stirred solution of 5.0 g of 6,7-dichloro-5-methoxy-2-methylbenzo[b]thiophen-3(2H)-one (5.0 g), in 120 ml of ethanol. Stirring is continued at room temperature for 1 hour and excess solvent is removed under reduced pressure. The residue is triturated with dilute sodium hydroxide solution and extracted 3 times with ether. The combined ether solution is washed thoroughly with water, dried and concentrated. Removal of ether leaves an oily residue which crystallized upon cooling. For analysis, a small sample was washed with pentane and dried at 60° C. to give 6,7-dichloro-2,3-dihydro-3-hydroxy-5-methoxy-2-methylbenzo[b]thiophene.

Workup

  1. customexcess solvent is removed under reduced pressure
  2. customThe residue is triturated with dilute sodium hydroxide solution
  3. extractionextracted 3 times with ether
  4. washThe combined ether solution is washed thoroughly with water
  5. customdried
  6. concentrationconcentrated
  7. customRemoval of ether
  8. customleaves an oily residue which
  9. customcrystallized
  10. temperatureupon cooling
  11. washFor analysis, a small sample was washed with pentane
  12. customdried at 60° C.

Sources & evidence

ORD record
ord-cca494339e3a435ba7ac9e1eb82b22cb
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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