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

HRID 1087005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087005
[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 ether layer is washed with 1 N 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 a).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-dba0003d33434f5dace37f274d1eeb23
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034381

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