1-Bromohexadecane → HCID 14350902, Verbindung

HRID 263833

Reaktionsgleichung

Reaktionsgleichung von HRID 263833
[H-].[Na+].[C:3]([O:22][CH2:23][CH:24]([CH2:26][OH:27])[OH:25])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>CN(C)C=O>[CH2:29]([O:27][CH2:26][CH:24]([CH2:23][O:22][C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[O:25][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH3:29])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Komponenten

5

Edukt 3

HCID 82131-BromohexadecaneHCID 24758Sodium hydrideHCID 28828273-Trityloxypropane-1,2-diol

Produkt 1

HCID 14350902HCID 14350902, VerbindungAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1H-nmr (200 MHz, CDCl3), 3.21 (2H, m), 3.65 (2H, m), 3.85 (1H, m), 7.4 (15H, m). ##STR17## Sodium hydride (prewashed with hexane, 60% oil dispersion, 0.79 g, 32.89 mmol) was stirred in dry dimethyl formamide (50 ml) under a stream of nitrogen. 1-trityl glycerol (5.0 g, 14.95 mmol) in dry dimethyl formamide (50 ml) was added carefully. The reaction was stirred at room temperature for 30 minutes before 1-bromohexadecane (9.13 g, 29.90 mmol) was added and the reaction was stirred at room temperature under a nitrogen atmosphere for 12 hours. The reaction mixture was carefully partitioned between dichloromethane (100 ml) and water (100 ml×3). The organic layer was washed successively with saturated NaHCO3 (100 ml) and brine (100 ml), dried over sodium sulphate and evaporated to yield the crude product, which was purified by column chromatography eluting with (40-60) light petroleum: ethyl acetate (230:20). Fractions containing product were evaporated to dryness to give 1,2-dihexadecyl-3-trityl glycerol (8.00 g, 10.21 mmol) 68% yield

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was carefully partitioned between dichloromethane (100 ml) and water (100 ml×3)
  3. washThe organic layer was washed successively with saturated NaHCO3 (100 ml) and brine (100 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto yield the crude product, which
  7. customwas purified by column chromatography
  8. washeluting with (40-60) light petroleum: ethyl acetate (230:20)
  9. additionFractions containing product
  10. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-01fff633c6774e4eb8c309ed33313eba
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05645883

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