Water → HCID 12968523, compound

HRID 1016366Notes

Reaction equation

HRID 1016366 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](S)=[CH:5][CH:4]=1.Br[CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=O.C([N:21](CC)CC)C.O[O:27][S:28]([O-:30])=O.[K+].[OH2:32]>C(O)C>[OH:32][NH:21][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][S:28]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:30])=[O:27]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 127654-MethoxybenzenethiolHCID 76300Ethyl 4-bromobutyrateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 12968523HCID 12968523, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part A: To a solution of 4-methoxybenzenethiol (2.5 g, 17.83 mmol) and ethyl 4-bromobutyrate (3.5 g, 17.83 mmol) in ethanol (50 mL) was cooled on an ice bath and triethylamine (2.73 mL, 19.61 mmol) was added. The solution stirred for 6 hours at ambient temperature. To this solution was added H2O (10 mL) and Oxone® (22 g, 35.7 mmol) and the solution stirred for 20 hours. The solution was filtered to remove excess Oxone® and the filtrate was concentrated in vacuo. The residue was dissolved into H2O and extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3 and saturated NaCl and dried over MgSO4. Chromatography (on silica, ethyl acetate/hexane) provided the sulfone as a white solid (2.41 g, 47%). HPLC purity: 97%.

Workup

  1. stirringthe solution stirred for 20 hours
  2. filtrationThe solution was filtered
  3. customto remove excess Oxone®
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved into H2O
  6. extractionextracted with ethyl acetate
  7. washThe combined organic layers were washed with saturated NaHCO3 and saturated NaCl
  8. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-fce89a9aaba54b7e872a786c90d3a86b
Source dataset
uspto-grants-2002_11
Patent number
US06476027B1

Reaction notes

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