Dimethyl Sulfoxide → HCID 21450777, compound

HRID 596153Notes

Reaction equation

HRID 596153 reaction equation
S(C)(C)=O.[H-].[Na+].[CH3:7][O:8][C:9]([O:26][CH3:27])([CH2:13][CH2:14][C:15](=[O:25])[CH2:16][CH2:17][CH2:18][CH:19]1[CH2:23][CH2:22][C:21](=[O:24])[O:20]1)[CH2:10][CH:11]=O.CO[CH2:30][CH2:31][O:32]C>O>[O:24]=[C:21]1[O:20][CH:19]([CH2:18][CH2:17][CH2:16][C:15](=[O:25])[CH2:14][CH2:13][C:9]([O:26][CH3:27])([O:8][CH3:7])[CH2:10]/[CH:11]=[CH:30]/[C:31](=[O:32])[CH2:11][CH2:10][CH2:9][CH2:13][CH3:14])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 21450765HCID 21450765, compound

Product 1

HCID 21450777HCID 21450777, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 70 parts of sulfinylbismethane with approximately 2 parts of a 50% dispersion of sodium hydride in mineral oil is added 11 parts of dimethyl (2-oxoheptyl) phosphonate. The resultant mixture is added, with stirring during 1 hour, to a solution of 10 parts of tetrahydro-β,β-dimethoxy-ε,5-dioxo-2-furannonanal in 52 parts of 1,2-dimethoxyethane at 0°-5° under nitrogen. Stirring is continued for 5 minutes longer, whereupon the reaction mixture is poured into 5 volumes of water, and the mixture thus obtained is extracted with benzene. The benzene extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is taken up in a 50:50 (by volume) mixture of ethyl acetate and hexane. The resultant solution is chromatographed on silica gel. Elution with a 75:25 (by volume) mixture of ethyl acetate and hexane affords, upon removal of solvent by vacuum distillation, (E)-1-(tetrahydro-5-oxofuran-2-yl)-7,7-dimethoxyhexadec-9-ene-4,11-dione as the residue, an oil. It has the formula ##STR11##

Workup

  1. customthe mixture thus obtained
  2. extractionis extracted with benzene
  3. extractionThe benzene extract
  4. washis washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationstripped of solvent by vacuum distillation
  7. additionThe residue is taken up in a 50:50 (by volume) mixture of ethyl acetate and hexane
  8. customThe resultant solution is chromatographed on silica gel
  9. washElution
  10. additionwith a 75:25 (by volume) mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f2390cb640fe461aa2f7fa71df31b490
Source dataset
uspto-grants-1977_03
Patent number
US04010169

Reaction notes

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