Pyridine → HCID 11097066, compound

HRID 1376312Notes

Reaction equation

HRID 1376312 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].N1C=CC=CC=1.[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]>ClCCl>[S:14]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6])([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

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

Product 1

HCID 11097066HCID 11097066, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-hexyn-1-ol (14 g), pyridine (20 ml) and dichloromethane (60 ml) were mixed and cooled to 0° C. Tosyl chloride (30 g:1.1 equivalent) was added portion wise over 20 minutes. After 5 hours at 0° C., the reaction was transferred to a separating funnel and washed with 2N HCl (2×50 ml) and saturated sodium bicarbonate (2×50 ml). These were back extracted with dichloromethane (1×25 ml) and the combined organic layers washed with water (1×50 ml). After drying (Na2SO4), the liquid was filtered off and the solvent evaporated to leave the product--33.4 g (93%)--of sufficient purity to be used for the next step.

Workup

  1. customthe reaction was transferred to a separating funnel
  2. washwashed with 2N HCl (2×50 ml) and saturated sodium bicarbonate (2×50 ml)
  3. extractionThese were back extracted with dichloromethane (1×25 ml)
  4. washthe combined organic layers washed with water (1×50 ml)
  5. dry with materialAfter drying (Na2SO4)
  6. filtrationthe liquid was filtered off
  7. customthe solvent evaporated
  8. customto leave the product--33.4 g (93%)

Sources & evidence

ORD record
ord-4f0435e422b348f4ae60943d2d59d9c0
Source dataset
uspto-grants-1997_09
Patent number
US05663042

Reaction notes

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