Water → HCID 54410579, compound

HRID 1650083Notes

Reaction equation

HRID 1650083 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH3:8][C:9]([CH3:17])([C:11]([CH:13]1[CH2:16][CH2:15][CH2:14]1)=[O:12])[CH3:10].O>CS(C)=O.O1CCCC1>[C:9]([C:11]1([CH:13]2[CH2:16][CH2:15][CH2:14]2)[CH2:4][O:12]1)([CH3:17])([CH3:10])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 1440585480875-33-8

Product 1

HCID 54410579HCID 54410579, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A suspension of sodium hydride (from 1.68 gms of petrol-washed 80% oil dispersion) in dimethylsulphoxide (40 mls) was stirred at 60° C. for 11/2 hours under a nitrogen atmosphere. The solution was cooled to 20° C., diluted with dry tetrahydrofuran (40 ml) and cooled to -5° C. A slurry of trimethylsulphonium iodide (11.42 gms) in dimethyl sulphoxide (30 mls) was added followed, after 10 minutes stirring, by a solution of the product of Stage 1 (4.9 g) in Tetrahydrofuran (30 mls). The mixture was stirred for 2 hours at -5° C., stood overnight at 20° C., and poured into water and extracted with petrol (30°-40° C.). The extracts were washed with brine, dried and evaporated to give 4.67 gms of yellow product. Gas chromatography showed 75% of a major component. The product was used without further purification.

Workup

  1. temperatureThe solution was cooled to 20° C.
  2. temperaturecooled to -5° C
  3. waitfollowed, after 10 minutes
  4. stirringThe mixture was stirred for 2 hours at -5° C.
  5. waitstood overnight at 20° C.
  6. extractionextracted with petrol (30°-40° C.)
  7. washThe extracts were washed with brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-34cc7e949111473295f228e9e714e50d
Source dataset
uspto-grants-1990_05
Patent number
US04923502

Reaction notes

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