Ethylene Glycol → Ethyl 2-(4-bromophenyl)-3-(2-(chloromethyl)-1,3-dioxolan-2-yl)propanoate

HRID 221971Notes

Reaction equation

HRID 221971 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][C:15](=[O:18])[CH2:16][Cl:17])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][C:15]2([CH2:16][Cl:17])[O:21][CH2:20][CH2:19][O:18]2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 59161523Ethyl 2-(4-bromophenyl)-5-chloro-4-oxopentanoate

Product 1

HCID 59161535Ethyl 2-(4-bromophenyl)-3-(2-(chloromethyl)-1,3-dioxolan-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 2-(4-bromophenyl)-5-chloro-4-oxopentanoate (1-2) (35 g, 105 mmol) and ethylene glycol (19.5 g, 315 mmol) in toluene (300 mL) was added para-toluenesulfonic acid (100 mg) and the reaction was heated to reflux with a dean stark trap for 6 hours. The reaction mixture was concentrated was purified by column chromatography eluting with 0-50% EtOAc/Hexane. The appropriate fractions were combined, concentrated, and the resulting solid was recrystallized from EtOAc and hexane to give ethyl 2-(4-bromophenyl)-3-[2-(chloromethyl)-1,3-dioxolan-2-yl]propanoate (1-3) as a white solid MS (M+H)+: 378.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux with a dean stark trap for 6 hours
  3. concentrationThe reaction mixture was concentrated
  4. customwas purified by column chromatography
  5. washeluting with 0-50% EtOAc/Hexane
  6. concentrationconcentrated
  7. customthe resulting solid was recrystallized from EtOAc and hexane

Sources & evidence

ORD record
ord-91872f4c84d54d1fab7a4e3873ce9901
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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