Sodium Hydroxide → (6-Phenylthio-2-pyridyl)methanol

HRID 27704

Reaction equation

HRID 27704 reaction equation
[C:1]1([S:7][C:8]2[N:13]=[C:12]([C:14](O)=[O:15])[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.O1CCCC1.[OH-].[Na+]>O1CCCC1.O.C(=O)([O-])[O-].[K+].[K+]>[C:1]1([S:7][C:8]2[N:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 233418226-Phenylthio-2-pyridylcarboxylic acid

Product 1

HCID 23324876(6-Phenylthio-2-pyridyl)methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a cooled solution of 6-phenylthio-2-pyridylcarboxylic acid (0.75 g, 3.25 mmol) in 10 ml of tetrahydrofuran in an ice bath is added dropwise a borane-tetrahydrofuran solution (6.7 ml total, 6.70 mmol) over a period of 20 minutes. The reaction mixture is stirred at RT overnight. 3 N aqueous sodium hydroxide (4 ml) is added slowly and stirring is continued for another 8 hours. The solution is diluted with water, saturated with solid potassium carbonate and extracted with water. The extract is washed with water, saturated NaHCO3 and brine and dried to yield (6-phenylthio-2-pyridyl)methanol.

Workup

  1. stirringstirring
  2. waitis continued for another 8 hours
  3. extractionextracted with water
  4. washThe extract is washed with water, saturated NaHCO3 and brine
  5. customdried

Sources & evidence

ORD record
ord-379baf98bf4c401181f67acb5585ab47
Source dataset
uspto-grants-1980_09
Patent number
US04223033

Linked notes

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