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

HRID 1531648Notes

Reaction equation

HRID 1531648 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

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 4-methylphenyl-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.

Workup

  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

Sources & evidence

ORD record
ord-5eb444f442124fcd931b761ee4e0aba0
Source dataset
uspto-grants-2001_03
Patent number
US06200971B1

Reaction notes

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