Pyridine → HCID 14805748, compound

HRID 1390185Notes

Reaction equation

HRID 1390185 reaction equation
[CH3:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:3][CH2:4][OH:5].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([O:5][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 6999991(3R)-3,7-Dimethyl-1-octanol

Product 1

HCID 14805748HCID 14805748, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 6.5 g (41 mmol) of (R)-3,7-dimethyl-1-octanol and 7.8 g (41 mmol) of p-toluenesulphonyl chloride in 50 ml of absolute chloroform is treated at 0° with 7.9 g (0.1 mol) of absolute pyridine. The mixture is subsequently stirred at 4° for 20 hours. For the working-up the mixture is poured on to 500 g of ice and extracted three times with chloroform. The combined organic phases are washed first with cold 1-N hydrochloric acid, then with saturated aqueous sodium bicarbonate solution and subsequently with saturated aqueous common salt solution. After drying over potassium carbonate and removal of the solvent under reduced pressure, the crude product is chromatographed on 300 g of silicagel with benzene. There are obtained 11.4 g (89%) of (R)-3,7-dimethyl-1-octanol p-toluenesulphonate; [α]D20 = +2.0 (c = 4.0, benzene).

Workup

  1. extractionextracted three times with chloroform
  2. washThe combined organic phases are washed first with cold 1-N hydrochloric acid
  3. dry with materialAfter drying over potassium carbonate and removal of the solvent under reduced pressure
  4. customthe crude product is chromatographed on 300 g of silicagel with benzene

Sources & evidence

ORD record
ord-b219d500b8854060898417dd0abe1d80
Source dataset
uspto-grants-1979_02
Patent number
US04138289

Reaction notes

Loading…