Dimethylformamide → 2-(1-Adamantyl)-4-bromo-1-decyloxybenzene

HRID 2081251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2081251
[H-].[Na+].[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[OH:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.I[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CN(C=O)C>C1COCC1.O>[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 163141-IododecaneHCID 24758Sodium hydrideHCID 46704942-(1-Adamantyl)-4-bromophenol

Produkt 1

HCID 136335522-(1-Adamantyl)-4-bromo-1-decyloxybenzeneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (80% in oil, 3.2 g, 104 mmol) in 100 ml of THF, there is slowly added a solution of 2-(1-adamantyl)-4-bromophenol (29 g, 95 mmol) in 200 ml of THF. The mixture is stirred until the evolution of gas ceases at which point 27.8 g (23 ml, 104 mmol) of 1-iododecane and 100 ml of DMF are added. The mixture is stirred for 12 hours at ambient temperature, poured into water, extracted with ether, dried and the solvents evaporated. The resulting residue is purified by passage through a silica column (eluant: heptane), yielding 40.7 g (96%) of 2-(1-adamantyl)-4-bromo-1-decyloxybenzene. Melting point: 69°-70° C.

Aufarbeitung

  1. additionare added
  2. extractionextracted with ether
  3. customdried
  4. customthe solvents evaporated
  5. customThe resulting residue is purified by passage through a silica column (eluant: heptane)

Quellen und Nachweise

ORD-Eintrag
ord-c9587630b7da4e0297c04eef2b1e1499
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05183889

Notizen zur Reaktion

Wird geladen…