Carbon Dioxide → Pent-4-yn-1-yl methanesulfonate

HRID 1734456Notes

Reaction equation

HRID 1734456 reaction equation
[CH:1]#[C:2][CH2:3][CH:4]([OH:6])C.C(=O)=O.[CH2:10](N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>CCOCC>[CH3:17][S:18]([O:6][CH2:4][CH2:3][CH2:2][C:1]#[CH:10])(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 929154-Pentyn-2-ol

Product 1

HCID 12476209Pent-4-yn-1-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To pentyne-4-ol (Farchan Chemical Co) (42.0 g: 0.5 mols) in 500 mL ether at -5° C. (dry ice bath) is added in a rapid dropwise fashion triethylamine (104.8 mL; 0.75 mols) diluted with 100 mL ether. While maintaining the temperature at or below 15° C. throughout, methane sulfonyl chloride, (94.2 mL; 0.70 mols) diluted with 100 mL ether, is added dropwise over 45 minutes. The thick suspension is stirred an additional 30 minutes, after which the precipitate is filtered. The filter cake is washed with ether and the combined ether layers washed twice with water, then once with brine. The ether layer is then dried over anhydrous magnesium sulfate and solvent removed under reduced pressure to yield the product as a pale yellow oil; yield 64 g (79%), which is used in the next step without further purification.

Workup

  1. additionis added dropwise over 45 minutes
  2. filtrationafter which the precipitate is filtered
  3. washThe filter cake is washed with ether
  4. washthe combined ether layers washed twice with water
  5. dry with materialThe ether layer is then dried over anhydrous magnesium sulfate and solvent
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-d5ef5c4864c940cdbd123dba77052096
Source dataset
uspto-grants-1996_07
Patent number
US05534484

Reaction notes

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