Potassium Carbonate → tert-Butyl [4-(cyanomethyl)phenoxy]acetate

HRID 840432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 840432
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:16]([O:15][C:13]([CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanideHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 15036608tert-Butyl [4-(cyanomethyl)phenoxy]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3 g of p-hydroxyphenylacetonitrile, 3.6 ml of t-butyl bromoacetate, 6.5 g of potassium carbonate in 45 ml of dimethylformamide is stirred at room temperature for 16 hours. After dilution with water the product is extracted with ether. The ethyl layer is washed with 1N sodium hydroxide, dried over magnesium sulfate and the solvent removed in vacuo to yield p-(t-butoxycarbonylmethoxy)-phenylacetonitrile which is reduced to p-(t-butoxycarbonylmethoxy)-2-phenethylamine with sodium borohydride/cobalt chloride as described for the starting material under (g).

Aufarbeitung

  1. extractionAfter dilution with water the product is extracted with ether
  2. washThe ethyl layer is washed with 1N sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e835b0c9d8bc4bc1890963e3fb510dd0
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06368573B1

Notizen zur Reaktion

Wird geladen…