Bromocyclopentane → Tert-butyl 2-cyclopentyl-2-(4-methylphenyl)acetate

HRID 377209

Reaktionsgleichung

Reaktionsgleichung von HRID 377209
CC([O-])(C)C.[K+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:10][CH:9]=1.[CH:22]1(Br)[CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C=O)C>[CH:22]1([CH:14]([C:11]2[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][CH:12]=2)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:26][CH2:25][CH2:24][CH2:23]1

Komponenten

5

Edukt 3

HCID 8728BromocyclopentaneHCID 12362014tert-Butyl (4-methylphenyl)acetateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 15234721Tert-butyl 2-cyclopentyl-2-(4-methylphenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

33.5 g (0.3 mol) of potassium tert-butylate are initially introduced into 100 ml of anhydrous DMF at 0° C., and 51.6 g (0.25 mol) of tert-butyl 4methylphenyl-acetate in 250 ml of anhydrous DMF are added dropwise. The mixture is stirred at 0° C. for 30 minutes, 32.2 ml (0.3 mol) of cyclopentyl bromide in 150 ml of anhydrous DMF are added dropwise at 5-15° C. and the mixture is stirred at 25° C. for 20 hours. After concentration, the residue is partitioned between water and diethyl ether and the ether phase is dried over sodium sulphate and concentrated. The product crystallizes out.

Aufarbeitung

  1. stirringthe mixture is stirred at 25° C. for 20 hours
  2. concentrationAfter concentration
  3. customthe residue is partitioned between water and diethyl ether
  4. dry with materialthe ether phase is dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe product crystallizes out

Quellen und Nachweise

ORD-Eintrag
ord-8a4fe0d7d6924c9aaf58e3e9983d1fa6
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025378

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