Trimethylstannane → 2-(p-Tolylsulfonyl)ethyltrimethylstannane

HRID 1283860Notes

Reaction equation

HRID 1283860 reaction equation
[CH:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4])=[CH2:2].[CH3:13][SnH:14]([CH3:16])[CH3:15]>O1CCCC1>[C:9]1([CH3:12])[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH2:2][Sn:14]([CH3:16])([CH3:15])[CH3:13])(=[O:5])=[O:4])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 12623TrimethylstannaneHCID 79665Benzene, 1-(ethenylsulfonyl)-4-methyl-

Product 1

HCID 129014332-(p-Tolylsulfonyl)ethyltrimethylstannaneYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in Example 1 was employed except that 7.74 g (42.5 mmoles) of 4-tolyl vinyl sulfone, 7.0 g (42.5 mmoles) of trimethyltin hydride and 10 ml of tetrahydrofuran were the reactants and solvent. The irradiation proceeded for 14.75 hours. Evaporation of solvent afforded an oil which crystallized on standing. Recrystallization of the product from cold petroleum ether gave 10.8 g of 2-(p-tolylsulfonyl)ethyltrimethylstannane, m.p. 55.5°-58°C. The presence of both the sulfonyl and trimethyltin groups was indicated by the strong infrared absorption bands at 1310 cm-1, 1295 cm-1, 1260 cm-1, 1145 cm-1 (--SO2 --) and 750 cm-1 ((CH3)3Sn) employing a KBr disc. Nuclear magnetic resonance spectroscopy (NMR) showed the following:

Workup

  1. customThe irradiation
  2. customEvaporation of solvent
  3. customafforded an oil which
  4. customcrystallized
  5. customRecrystallization of the product from cold petroleum ether

Sources & evidence

ORD record
ord-cf89e8efa9c74f25aab0f26972698b13
Source dataset
uspto-grants-1976_08
Patent number
US03976672

Reaction notes

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