Pyridine → Phenyl [4-(tetradecyloxy)phenyl]methyl carbonate

HRID 1728872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728872
[CH2:1]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].N1C=CC=CC=1.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:31](=[O:32])([O:21][CH2:20][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:23][CH:22]=1)[O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 100873844-Tetradecyloxybenzyl alcohol

Produkt 1

HCID 10411003Phenyl [4-(tetradecyloxy)phenyl]methyl carbonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. mixture of 9.0 g of product from Example 19, 4.44 g of pyridine and 70 ml of methylene chloride is added, dropwise, 5.28 of phenyl chloroformate. The reaction is stirred at 0° C. for 15 minutes; followed by room temperature for 30 minutes. The mixture is poured into saturated sodium bicarbonate and the aqueous layer is extracted with methylene chloride. The combined organic layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 0-5% ethyl acetate/hexane) to give 12.6 g of colorless prisms.

Aufarbeitung

  1. additionis added
  2. waitfollowed by room temperature for 30 minutes
  3. extractionthe aqueous layer is extracted with methylene chloride
  4. washThe combined organic layers are washed with saturated sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (silica gel: 0-5% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1503961f4c6f419ebbcadc25cd59dbee
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05328921

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