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

HRID 1457616Notes

Reaction equation

HRID 1457616 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>[CH2:22]1[CH2:26][CH2:25][CH2:24][CH:23]1[CH:14]([C:11]1[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][CH:12]=1)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

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 the compound from Example V 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. Yield: 67 g (97.5% of theory) Melting point=51°-53° C.

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-c4409ef58b89402dba321235fb076593
Source dataset
uspto-grants-1998_12
Patent number
US05849751

Reaction notes

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