Pyridine → HCID 56638727, compound

HRID 2309131Notes

Reaction equation

HRID 2309131 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(Cl)(=O)=O)=[CH:9][CH:8]=1.[C:18]([O-:21])(O)=[O:19].[Na+].[S:23]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)([O-:26])(=[O:25])=[O:24].[CH3:34][CH2:35][O:36][CH2:37][CH3:38]>O>[CH2:35]([O:36][CH2:37][C@H:38]1[C@H:17]([O:19][CH:18]2[CH2:5][CH2:4][CH2:3][CH2:2][O:21]2)[CH2:7][C@H:12]([O:24][S:23]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C@@H:11]1[CH2:10][CH:9]=[CH2:8])[C:34]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 85570p-ToluenesulfonateHCID 516892Sodium Bicarbonate

Product 1

HCID 56638727HCID 56638727, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 12.5 g. of the alcohol prepared according to Reference Example 1(c) in 36 ml. of pyridine is combined with 13.6 g. of p-toluenesulfonyl chloride and agitated for 2 days at room temperature under argon. The mixture is then combined with 6 ml. of ice water, stirred for 2 hours at room temperature, diluted with 0.6 l. of ether, and shaken, in succession, with water, ice-cold 4% sulfuric acid, water, 5% NaHCO3 solution, and three times with water. The mixture is dried over magnesium sulfate and evaporated under vacuum, thus obtaining 17.3 g. of the tosylate as a colorless oil

Workup

  1. additiondiluted with 0.6 l
  2. dry with materialThe mixture is dried over magnesium sulfate
  3. customevaporated under vacuum
  4. customthus obtaining 17.3 g

Sources & evidence

ORD record
ord-077163dab8e8466da65b0b7c7b6d6a6a
Source dataset
uspto-grants-1987_09
Patent number
US04692464

Reaction notes

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