Ethanol → 7-Methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 1289492Notes

Reaction equation

HRID 1289492 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[CH:7]=[CH:6][NH:5]1.C(O)C>O>[CH3:3][CH:4]1[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[CH2:7][CH2:6][NH:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 18921799HCID 18921799, compound

Product 1

HCID 145481697-Methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridineYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride(4.4 g, 116 mmol) was added portionwise at room temperature to a mixture solution of 7-methyl-6,7-dihydrothieno[2,3-c]pyridine(10.5 g, 69.4 mmol) prepared in the above Step 2 and ethanol(100 ml). After stirring for 1 hour, the reaction mixture was diluted with water, and extracted with dichloromethane. The combined dichloromethane layers were dried over magnesium sulfate and concentrated to give 10.34 g of the titled compound. (Yield: 97%)

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined dichloromethane layers were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c9cf938a6fb744f08f9ed50bda957f82
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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