Tetrahydrofuran → 2-Phenyl-3-sulfonlyphenyl-propenoic acid, methyl ester

HRID 440379Notes

Reaction equation

HRID 440379 reaction equation
[C:1]1([S:7](CP(=O)(OCC)OCC)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:34]([C:42]([O:44][CH3:45])=[O:43])(=O)[C:35]1C=CC=CC=1.C(OCC)(=O)C.[CH3:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]>>[C:54]1([CH:2]2[C:1](=[S:7](=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[C:3]2[C:34](=[CH2:35])[C:42]([O:44][CH3:45])=[O:43])[CH:53]=[CH:52][CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 84835Methyl phenylglyoxalateHCID 2733832Lithium Hexamethyldisilazide2×HCID 10891636Diethyl ((phenylsulfonyl)methyl)phosphonateHCID 21226206Ethyl acetate hexane3×

Product 1

HCID 867494882-Phenyl-3-sulfonlyphenyl-propenoic acid, methyl ester

Procedure

Combine diethyl phenylsulphonylmethylphosphonate (T. A. Blumenkopf Synth. Commun. 26, 139-147, (1986)) (117.0 g, 400 mmol) and tetrahydrofuran (500 mL). Cool in an ice-bath. Add lithium bis(trimethylsilyl)amide (480 mL, 1M in tetrahydrofuran, 480 mmol). Stir for 30 minutes after the addition of lithium bis(trimethylsilyl)amide, then add methyl benzoylformate (72.0 g, 439 mmol). Warm to ambient temperature and stir for 2 hours. Partition between water and ethyl acetate. Extract the aqueous layer with ethyl acetate. Combine the organic layers, dry over magnesium sulfate and evaporate in vacuo to give an oil. Triturate with cyclohexane to give a solid. Chromatograph the solid on silica gel eluting sequentially with 10% ethyl acetate/hexane, 15% ethyl acetate/hexane, and 33% ethyl acetate/hexane. Evaporation of the product containing fractions give a solid. Recrystallize form ethyl acetate/hexane to give 2-phenyl-3-sulfonylphenyl-propenoic acid, methyl ester as a solid. Elem. Anal calculated for C16H14O4S: C, 63.56; H, 4.67. Found: C, 63.25; H, 4.70.

Workup

  1. temperatureCool in an ice-bath
  2. stirringstir for 2 hours
  3. customPartition between water and ethyl acetate
  4. extractionExtract the aqueous layer with ethyl acetate
  5. dry with materialdry over magnesium sulfate
  6. customevaporate in vacuo
  7. customto give an oil
  8. customTriturate with cyclohexane
  9. customto give a solid
  10. customEvaporation of the product
  11. additioncontaining fractions
  12. customgive a solid
  13. customRecrystallize
  14. customform ethyl acetate/hexane

Sources & evidence

ORD record
ord-659bde28daac47cd9a005b90cab63769
Source dataset
uspto-grants-1996_05
Patent number
US05519048

Reaction notes

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