Dimethylformamide → 3-[6-(Triphenylmethoxy)hexyloxy]-2-methylenepropan-1-ol

HRID 2166440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2166440
[H-].[Na+].CN(C)[CH:5]=[O:6].Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[C:17]1([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:15][CH2:14][C:13](=[CH2:12])[CH2:5][OH:6])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 11955063Benzene, 1,1',1''-[[(6-chlorohexyl)oxy]methylidyne]tris-

Produkt 1

HCID 230396333-[6-(Triphenylmethoxy)hexyloxy]-2-methylenepropan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Sodium hydride (from 55-60% oil dispersion (0.52 g) washed with pentane (3×3 ml)), dry dimethylformamide (20 ml), and 2-metyylenepropane-1,3-diol (1.0 g) were mixed. After 1 hour when H2 -evolution had ceased 1-chloro-6-(triphenylmethoxy)hexane (4.2 g) was added, and the mixture was stirred for 3 hours at 85° C. After cooling water (20 ml) was carefully added, and the mixture was extracted with ether (2×100 ml). The ether extracts were washed with water (100 ml), dried over magnesium sulfate and evaporated to dryness in vacuo. The product was purified through a column of silica gel 60 (70-230 mesh, 40 g) eluting with ether. Futher purification was achieved by chromatography on Waters PrepLC®/System 500A using a prepPAK®-500/SILICA cartridge with ether/pentane 1:2 followed by ether/pentane 1:1 as eluent.

Aufarbeitung

  1. additionwas carefully added
  2. extractionthe mixture was extracted with ether (2×100 ml)
  3. washThe ether extracts were washed with water (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness in vacuo
  6. customThe product was purified through a column of silica gel 60 (70-230 mesh, 40 g)
  7. washeluting with ether
  8. customFuther purification

Quellen und Nachweise

ORD-Eintrag
ord-0d383f45eb3c47559b2a5d2a8c8d6fa7
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04945098

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