Chloroacetone → HCID 66764943, compound

HRID 1466816Notes

Reaction equation

HRID 1466816 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([SH:13])[CH:6]=1)[CH3:2].C(N(CC)CC)C.Cl[CH2:23][C:24](=[O:26])[CH3:25].CCOC(C)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([S:13][CH2:23][C:24](=[O:26])[CH3:25])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66764668HCID 66764668, compound

Product 1

HCID 66764943HCID 66764943, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Mercapto-4-methoxy-benzoic acid ethyl ester (1.29 g, 6.08 mmol) and triethylamine (2.12 mL, 15.19 mmol) were dissolved in THF (20 mL) at 0° C. Chloroacetone (0.58 mL, 7.29 mmol) was then added and the reaction stirred at room temperature for 30 minutes. It was then allowed to slowly warm to room temperature and stirred an additional 30 minutes. Standard aqueous workup followed by silica gel chromatography (0-70% EtOAc in hexanes) gave the title compound.

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringstirred an additional 30 minutes

Sources & evidence

ORD record
ord-3720f8e87e0343edb07455a2d4f8fa81
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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