Potassium Carbonate → 2-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitrophenyl]propanoic acid methyl ester

HRID 987267Notes

Reaction equation

HRID 987267 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]CS([O-])(=O)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH3:19][O:20][C:21](=[O:37])[CH:22]([O:34][CH2:35][CH3:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][C:25]=1[N+:31]([O-:33])=[O:32].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCCC>C(#N)C>[CH3:19][O:20][C:21](=[O:37])[CH:22]([O:34][CH2:35][CH3:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:13][CH2:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=2)=[CH:26][C:25]=1[N+:31]([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 21899848Ethylacetate heptaneHCID 227084532-(4-Methylsulfonyloxyphenyl)ethylmethanesulfonate2×HCID 538988402-Ethoxy-3-(4-hydroxy-2-nitrophenyl)propanoic acid methyl ester

Product 1

HCID 571861342-Ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitrophenyl]propanoic acid methyl esterYield 81.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-Methanesulfonyloxyphenyl)ethylmethanesulfonate (1.14 g; 3.87 mmole), 2-ethoxy-3-(4-hydroxy-2-nitrophenyl)propanoic acid methyl ester (1.04 g; 3.86 mmole) and potassium carbonate (1.07 g; 7.75 mmole) were mixed in acetonitrile (approx. 100 ml). The reaction mixture was heated to reflux for 6 hours and according to TLC the reaction was not complete. Another portion of 2-(4-methanesulfonyloxyphenyl)ethylmethanesulfonate (0.2 g; 0.68 mmole) was added. The reaction mixture was heated to reflux over night, and then evaporated to dryness. Ethyl acetate and water were added into the residue. The phases were separated and the organic phase was washed with brine, dried with magnesium sulfate and evaporated. Chromatography of the crude product on silica gel with a gradient of ethyl acetate/heptane as eluant gave 1.47 g (81% yield) of 2-ethoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)-2-nitrophenyl]propanoic acid methyl ester.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux over night
  5. customevaporated to dryness
  6. additionEthyl acetate and water were added into the residue
  7. customThe phases were separated
  8. washthe organic phase was washed with brine
  9. dry with materialdried with magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-914e7c65100a48b2a995e2e27c12a5c1
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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