Pyridine → HCID 11097066, compound

HRID 461925Notes

Reaction equation

HRID 461925 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:18]([OH:24])[CH2:19][CH2:20][CH2:21][C:22]#[CH:23]>O>[S:7]([O:24][CH2:18][CH2:19][CH2:20][CH2:21][C:22]#[CH:23])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 702345-Hexyn-1-ol

Product 1

HCID 11097066HCID 11097066, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In this preparation 1.0 mole of p-toluenesulfonyl chloride is dissolved in 700 ml. of pyridine at 0° C, under nitrogen, and then 0.5 mole of hex-5-yn-1-ol is added dropwise. The mixture is stirred for 2 hours and then 10 ml. of water is added slowly, keeping the temperature below 10° C. The pyridine is then removed by evaporation under vacuum and the residue poured into 1 liter of ethyl acetate, then washed twice with excess 2N aqueous hydrochloric acid, and then with water. The organic layer is separated and dried over anhydrous magnesium sulfate, filtered, and the filtrate then evaporated to dryness, under vacuum, affording hex-5-yn-1-ol tosylate.

Workup

  1. dissolutionis dissolved in 700 ml
  2. customthe temperature below 10° C
  3. customThe pyridine is then removed by evaporation under vacuum
  4. additionthe residue poured into 1 liter of ethyl acetate
  5. washwashed twice with excess 2N aqueous hydrochloric acid
  6. customThe organic layer is separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate then evaporated to dryness, under vacuum

Sources & evidence

ORD record
ord-7692b7b9ec1541ea8b7726788f8838d0
Source dataset
uspto-grants-1977_12
Patent number
US04064257

Reaction notes

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