Methanol → 6-Azidohex-1-yne

HRID 461926Notes

Reaction equation

HRID 461926 reaction equation
S(OCCCCC#C)([C:4]1[CH:10]=[CH:9][C:7](C)=[CH:6][CH:5]=1)(=O)=O.[N-:18]=[N+:19]=[N-:20].[Na+].CO>O>[N:18]([CH2:10][CH2:9][CH2:7][CH2:6][C:5]#[CH:4])=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 33557Sodium AzideHCID 11097066HCID 11097066, compound

Product 1

HCID 213926596-Azidohex-1-yne

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 0.397 mole of hex-5-yn-1-ol tosylate; 0.76 mole of sodium azide; and one liter of methanol and 200 ml. of water is stirred at 60° C for 4 hours. The mixture is then evaporated under vacuum to remove the majority of the methanol and the remaining concentrate then poured into 500 ml. of ethyl ether, and then extracted three times with water, and dried over anhydrous magnesium sulfate and filtered. The filtrate is then evaporated, under vacuum, affording 1-azidohex-5-yne as a residue.

Workup

  1. customThe mixture is then evaporated under vacuum
  2. customto remove the majority of the methanol
  3. concentrationthe remaining concentrate
  4. additionthen poured into 500 ml
  5. extractionof ethyl ether, and then extracted three times with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate is then evaporated, under vacuum

Sources & evidence

ORD record
ord-46cf7dadc21a466e980df03c36b439ac
Source dataset
uspto-grants-1977_12
Patent number
US04064257

Reaction notes

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