Dimethyl Sulfoxide → HCID 21406503, compound

HRID 1729893Notes

Reaction equation

HRID 1729893 reaction equation
[H-].[Na+].[H][H].C([C:7]1[C:19]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][C:8]=1[C:20](=O)[C:21]([OH:23])=[O:22])C.[CH3:25]S(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:25]=[C:20]([C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:18][C:19]=2[CH:7]=1)[C:21]([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 70633383HCID 70633383, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21406503HCID 21406503, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

A mixture of sodium hydride (0.48g.) and dimethylsulfoxide (5ml.) is stirred and heated at 70°-80° until the evolution of hydrogen ceases. The cooled solution is treated with methyltriphenylphosphonium bromide (7.14g.) in dimethylsulfoxide (10ml.), stirred for 10 minutes and treated with ethyl fluorene-2-glyoxylic acid (5.32g.). The reaction mixture is stirred for 1 hr., the solvent evaporated and the residue extracted with ether after the addition of water. The ether extracts are washed with water, dried (MgSO4) and evaporated. The residue is hydrolyzed by refluxing it in 50% methanol (50ml.) containing potassium hydroxide (5g.) for 3 hr. The reaction mixture is concentrated, acidified and extracted with ether. The ether extracts are washed with water, dried (MgSO4) and evaporated to give the title compound.

Workup

  1. stirringstirred for 10 minutes
  2. stirringThe reaction mixture is stirred for 1 hr
  3. custom, the solvent evaporated
  4. extractionthe residue extracted with ether
  5. additionafter the addition of water
  6. washThe ether extracts are washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. temperatureby refluxing it in 50% methanol (50ml.)
  10. additioncontaining potassium hydroxide (5g.) for 3 hr
  11. concentrationThe reaction mixture is concentrated
  12. extractionextracted with ether
  13. washThe ether extracts are washed with water
  14. dry with materialdried (MgSO4)
  15. customevaporated

Sources & evidence

ORD record
ord-a043b0f6fa3142589b267d6907a0d305
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

Loading…