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

HRID 25153

Reaktionsgleichung

Reaktionsgleichung von HRID 25153
CC(C)([O-])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-butoxide are initially introduced into 100 ml of anhydrous DMF at 0° C., and 51.6 g (0.25 mol) of the compound from Example XX in 250 ml of anhydrous DMF are added dropwise. The mixture is stirred at 0° C. for 30 min and 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 h. After concentrating, 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 h
  2. concentrationAfter concentrating
  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-f849e1c730c94e5db84ce2e7ae990baa
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858622B2

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