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

HRID 864921

Reaktionsgleichung

Reaktionsgleichung von HRID 864921
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureWhile maintaining the temperature at or below 15° C. throughout
  2. additionis added dropwise over 45 minutes
  3. filtrationafter which the precipitate is filtered
  4. washThe filter cake is washed with ether
  5. washthe combined ether layers washed twice with water
  6. dry with materialThe ether layer is then dried over anhydrous magnesium sulfate and solvent
  7. customremoved under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b7f7f22e6c474aeab2e69a3c216ef1ef
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565411

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