Hydrochloric Acid → 3-Dodecyl-5-methylisoxazole

HRID 264106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 264106
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:4]=1.[BH4-].[Na+].Cl>CS(C)=O>[CH2:8]([C:5]1[CH:4]=[C:3]([CH3:2])[O:7][N:6]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 105443765-(Bromomethyl)-3-dodecylisoxazole

Produkt 1

HCID 104913863-Dodecyl-5-methylisoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A suspension of 5-(bromomethyl)-3-dodecylisoxazole (9.99 g, 0.0302 mol) in dimethylsulfoxide (100 mL) was warmed to give a cloudy solution and allowed to cool. When the temperature reached +35° C., sodium borohydride (1.2 g, 0.032 mol) was added in one portion, and the mixture was stirred for 3 days under nitrogen at room temperature. The mixture was poured into 0.1M HCl (900 mL) and extracted with ether. The organic layer was washed (saturated NaCl), dried (MgSO4), and rotoevaporated. The residue was chromatographed on silica gel (160 g, 70-230 mesh) using petroleum ether-acetone (29:1, 10×200 mL) as eluent. Fraction 6 was rotoevaporated and dried in vacuo to give a white solid; yield 3.96 g (52%); mp 35°-38° C.

Aufarbeitung

  1. temperaturewas warmed
  2. customto give a cloudy solution
  3. temperatureto cool
  4. customreached +35° C.
  5. extractionextracted with ether
  6. washThe organic layer was washed (saturated NaCl)
  7. dry with materialdried (MgSO4)
  8. customThe residue was chromatographed on silica gel (160 g, 70-230 mesh)
  9. customdried in vacuo
  10. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-8771b1b62d9f40e3834d67fd7aad81cb
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646170

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