Isopropanol → HCID 18427232, Verbindung

HRID 843511

Reaktionsgleichung

Reaktionsgleichung von HRID 843511
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[H-].[Na+].S(C1C=CC(C)=CC=1)(O[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=O)=O.[CH:36](O)([CH3:38])[CH3:37]>O1CCCC1>[CH2:37]([O:4][CH2:3][CH:2]([NH2:1])[CH2:5][O:6][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])[CH2:36][CH2:38][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 68294SerinolHCID 801711-Hexadecanol, 1-(4-methylbenzenesulfonate)

Produkt 1

HCID 18427232HCID 18427232, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 2-amino-1,3-propanediol (Serinol: Aldrich Chem. Co., Milwaukee, Wis.; Catalog No. 35,789-8) in tetrahydrofuran (THF) is added dropwise with vigorous stirring to a slurry of sodium hydride in THF over a period of 1-2 hrs. The reaction mixture is stirred for an additional 30 minutes to 1 hr at room temperature. Hexadecyl tosylate in THF is added dropwise to the mixture with vigorous stirring over a period of 1-1.5 hrs. The reaction mixture is stirred at room temperature for 1 hr and worked up by addition of isopropanol to destroy excess sodium hydride. The reaction mixture is extracted with chloroform (3×100 mL) and the combined chloroform layers are washed with water (2×50 mL), saturated NaCl (1×50 mL) and dried (MgSO4). The dried chloroform layer is evaporated under vacuum to afford the product as an off-white solid.

Aufarbeitung

  1. stirringwith vigorous stirring over a period of 1-1.5 hrs
  2. stirringThe reaction mixture is stirred at room temperature for 1 hr
  3. customto destroy excess sodium hydride
  4. extractionThe reaction mixture is extracted with chloroform (3×100 mL)
  5. washthe combined chloroform layers are washed with water (2×50 mL), saturated NaCl (1×50 mL)
  6. dry with materialdried (MgSO4)
  7. customThe dried chloroform layer is evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fdef1f05acf6447291aeac43f2794c5e
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06379930B1

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