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Trityl chloride → 1,1,1-Triphenyl-2,5,8,11-tetraoxatridecan-13-OL

HRID 1818094
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1818094
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].C(N(CC)CC)C.[C:21]1([C:27](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[C:21]1([C:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
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Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 8200Tetraethylene GlycolHCID 8471Triethylamine

Produkt 1

HCID 115465991,1,1-Triphenyl-2,5,8,11-tetraoxatridecan-13-OLAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To tetraethylene glycol (213.65 g, 1.1 mol) and triethylamine (20.24 g, 27.8 ml, 200 mmol) in dry dichloromethane (1500 ml) was added dropwise triphenylmethyl chloride (27.88 g, 100 mmol) in dry dichloromethane (500 ml). This solution was left to stir under argon at room temperature for 24 hours. After 24 hours, the reaction was concentrated in vacuo to give a mixture of product and starting material as a yellow oil. This oil was then re-dissolved in dichloromethane (1000 ml), partitioned with sat. aq. NaHCO3 (500 ml), water (3×400 ml) and finally sat. aq. NaCl (500 ml). The organic layer was separated, dried over anhydrous sodium sulphate and concentrated in vacuo to give the title compound as a yellow oil (42.2 g, 95%) which was used without further purification.

Aufarbeitung

  1. waitThis solution was left
  2. waitAfter 24 hours
  3. concentrationthe reaction was concentrated in vacuo
  4. customto give
  5. additiona mixture of product
  6. custompartitioned with sat. aq. NaHCO3 (500 ml), water (3×400 ml) and finally sat. aq. NaCl (500 ml)
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-280a06e1faf14c1bb73f514356487fe8
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07598421B2

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