1,5-Dibromopentane → Dibenzyl cyclohexane-1,1-dicarboxylate

HRID 1860509Notes

Reaction equation

HRID 1860509 reaction equation
[C:1]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:13])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[C:2]1([C:1]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])([C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 84754Dibenzyl malonate

Product 1

HCID 15416540Dibenzyl cyclohexane-1,1-dicarboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of dibenzyl malonate (40 g, 161 mmol), 1,5-dibromopentane (22 mL, 161 mmol) and potassium carbonate (56 g, 402 mmol) in 300 mL of DMSO was stirred for 48 h in an oil bath at 50° C. The mixture was diluted with water and extracted with ethyl acetate (2×). The combined organic portions were dried over magnesium sulfate and concentrated. Flash chromatography (400 g silica, 15/1 hexane/EtOAc) gave the desired product. 1H NMR (500 MHz, CDCl3) δ1.4-1.5 (m, 1H), 1.52-1.6 (m, 5H), 2.03-2.1 (m, 4H), 5.13 (s, 4H), 7.22-7.38 (m, 10H).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. dry with materialThe combined organic portions were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c963cf1e3c624ffd801af05a9683f76b
Source dataset
uspto-grants-2003_03
Patent number
US06531484B2

Reaction notes

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