Water → HCID 12901378, compound

HRID 971700Notes

Reaction equation

HRID 971700 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7]([O-:9])=[O:8])=[CH:3][CH:2]=1.[Na+].O.Br[CH2:14][CH2:15][CH2:16][CH2:17][Sn:18]([CH3:21])([CH3:20])[CH3:19]>[Br-].C([P+](CCCC)(CCCC)CCCCCCCCCCCCCCCC)CCC.C1(C)C=CC=CC=1>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S:7]([CH2:14][CH2:15][CH2:16][CH2:17][Sn:18]([CH3:21])([CH3:20])[CH3:19])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2723791Sodium p-toluenesulfinateHCID 12901377(4-Bromobutyl)(trimethyl)stannane

Product 1

HCID 12901378HCID 12901378, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 1140TolueneSolvent

Procedure

Into a 125 ml single-necked round bottom flask fitted with a teflon coated magnetic stir bar and a reflux condenser was charged 4.45 g of sodium p-toluenesulfinate, 20 ml water, 10 ml toluene, 7 g of 75% 4-bromobutyltrimethylstannane and 0.44 g of tri-n-butylhexadecylphophonium bromide. The mixture was refluxed for 2.5 hours with rapid stirring. On cooling, the organic phase was separated, dried over anhydrous magnesium sulfate and stripped of solvent on a rotary evaporator. The oil residue was distilled two times through a short path distillation head. The second distillation afforded 3.3 g of 4-(-p-tolylsulfonyl)butyltrimethylstannane, b.p. 136°-140° C. (1× 10-3 mm Hg). The presence of both the sulfonyl and trimethyltin moieties was indicated by strong infrared absorption bands at 1315 cm-1, 1300 cm-1, 1142 cm-1 (--SO2 --) and 765 cm-1 [(CH3)3Sn--]. NMR spectroscopy showed the following:

Workup

  1. customInto a 125 ml single-necked round bottom flask fitted with a teflon coated magnetic stir bar and a reflux condenser
  2. temperatureThe mixture was refluxed for 2.5 hours with rapid stirring
  3. temperatureOn cooling
  4. customthe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customstripped of solvent on a rotary evaporator
  7. distillationThe oil residue was distilled two times
  8. distillationthrough a short path distillation head
  9. distillationThe second distillation

Sources & evidence

ORD record
ord-0bc7d5a5b7a7498b866763d85d5cc71f
Source dataset
uspto-grants-1979_07
Patent number
US04160846

Reaction notes

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