Benzyl Bromide → HCID 57295455, compound

HRID 256395Notes

Reaction equation

HRID 256395 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[S:12](=[O:17])(=[O:16])[CH2:11][CH2:10][CH2:9]2.C([Li])CCC.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[CH2:23]([CH:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH:2]=[O:3])[CH:7]=2)[S:12]1(=[O:16])=[O:17])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 57166565HCID 57166565, compoundHCID 178418339Butyllithium

Product 1

HCID 57295455HCID 57295455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 254 mg (1.0 mmole) 6-(1,3-dioxolan-2-yl)-1,1-dioxothiachroman in 10 ml tetrahydrofuran was cooled to 0° C. and 1.15 mmole of 2.3M n-butyllithium was added dropwise. The resulting red solution was stirred for 30 minutes at 0° C., 137 microliters (1.15 mmole) benzyl bromide was added and stirring continued at 0° C. for one hour, then at room temperature for two hours. The reaction was quenched by addition of citric acid. The mixture was taken up in ethyl ether, washed with brine, dried (MgSO4) and the solvents evaporated. The residue was taken up in 15 ml tetrahydrofuran, 10 ml 3.5% aqueous perchloric acid added and the mixture stirred overnight. Extraction with ethyl ether, washing with brine, drying (MgSO4) and evaporation of solvent gave the title compound as an oil, Rf 0.6 on silica gel TLC (9:1 methylene chloride/ethyl ether).

Workup

  1. stirringstirring
  2. waitcontinued at 0° C. for one hour
  3. waitat room temperature for two hours
  4. customThe reaction was quenched by addition of citric acid
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvents evaporated
  8. addition10 ml 3.5% aqueous perchloric acid added
  9. stirringthe mixture stirred overnight
  10. extractionExtraction with ethyl ether
  11. washwashing with brine
  12. customdrying
  13. custom(MgSO4) and evaporation of solvent

Sources & evidence

ORD record
ord-d2d2d3bd62714b468e6efc701d0b349d
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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