Triethylamine → 2-[(Methylsulfonyl)oxy]-5-hexynenitrile

HRID 236028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236028
[OH:1][CH:2]([CH2:5][CH2:6][C:7]#[CH:8])[C:3]#[N:4].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:1][CH:2]([CH2:5][CH2:6][C:7]#[CH:8])[C:3]#[N:4])(=[O:19])=[O:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 130449482-Hydroxy-5-hexynenitrile

Produkt 1

HCID 130449492-[(Methylsulfonyl)oxy]-5-hexynenitrileAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A mixture of 2-hydroxy-5-hexynenitrile (8.0 g, 73.3 mmol) and dry triethylamine (10.1 g, 0.1 mol) in 50 ml of dry CH2Cl2 was treated with a solution of methanesulfonyl chloride (10.3 g, 90 mmol) in 50 ml of CH2Cl2, at 0° C. for 11/2 h. The reaction mixture was diluted with CH2Cl2, washed twice with cold 1.0N H2SO4, twice with water, and dried over MgSO4. The filtered CH2Cl2 solution was concentrated at 40° C./30 mm to give 12 g of pale yellow liquid. Purification of this material on 220 g of silica gel and eluted with ether-petroleum ether (1:1 parts by volume) gave 8.7 g (56% by weight yield from pentynal) of 2-[(methylsulfonyl)]-5-hexynenitrile as a colorless liquid.

Aufarbeitung

  1. washwashed twice with cold 1.0N H2SO4, twice with water
  2. dry with materialdried over MgSO4
  3. concentrationThe filtered CH2Cl2 solution was concentrated at 40° C./30 mm

Quellen und Nachweise

ORD-Eintrag
ord-eb0262456984467ab69dbcd0f0e49a68
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642364

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