1-Iodooctadecane → HCID 20218649, Verbindung

HRID 235712

Reaktionsgleichung

Reaktionsgleichung von HRID 235712
[OH:1][CH2:2][CH:3]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[H-].[Na+].[CH2:18](I)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>CN(C)C=O.O1CCCC1.CCOCC>[CH2:35]([O:1][CH2:2][CH:3]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18]

Komponenten

7

Edukt 3

HCID 124021-IodooctadecaneHCID 24758Sodium hydrideHCID 20219052N-[1-(hydroxymethyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]acetamide

Produkt 1

HCID 20218649HCID 20218649, VerbindungAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of about 10.85 g of N-[1-(hydroxymethyl)-2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]acetamide in about 240 ml of dry dimethylformamide was added dropwise to a suspension of about 3.12 g of about 50% sodium hydride (pre-washed with anhydrous ether). After stirring about one hour a solution of about 22.8 g of octadecyl iodide in about 150 ml of tetrahydrofuran was added, stirring was continued for about 24 hours, then the mixture was diluted with ether and washed with a minimum amount of brine. The organic layer was dried, the solvents evaporated and the crude material purified by chromatography on silica gel, eluting with ethyl acetate:hexane:ethanol (about 1:1:0.2), giving about 8 g of the desired title compound, mp 52°-55° C.

Aufarbeitung

  1. additionwas added
  2. washwashed with a minimum amount of brine
  3. customThe organic layer was dried
  4. customthe solvents evaporated
  5. customthe crude material purified by chromatography on silica gel
  6. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ad0c1099a691405d99372083342fd252
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640913

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