Trimethylstannane → [2-(4-tert-Butylbenzene-1-sulfonyl)ethyl](trimethyl)stannane

HRID 1283859Notes

Reaction equation

HRID 1283859 reaction equation
[CH:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4])=[CH2:2].[CH3:16][SnH:17]([CH3:19])[CH3:18]>[Hg].C1(C)C=CC=CC=1>[C:12]([C:9]1[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH2:2][Sn:17]([CH3:19])([CH3:18])[CH3:16])(=[O:5])=[O:4])=[CH:7][CH:8]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 12623TrimethylstannaneHCID 8793221-Tert-butyl-4-(ethenesulfonyl)benzene

Product 1

HCID 326737[2-(4-tert-Butylbenzene-1-sulfonyl)ethyl](trimethyl)stannaneYield 68.9%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 1140TolueneSolvent

Procedure

An 80 ml, two-necked, pyrex glass Schlenk reaction tube containing a Teflon coated magnetic stir bar was swept thoroughly with nitrogen and maintained in an air-free condition. The tube was charged with 9.5 g (42.5 mmoles) of 4-t-butylphenyl vinyl sulfone, 7.0 g (42.5 mmoles) of trimethyltin hydride and 10 ml. of toluene, stoppered, and placed in a 20°C water bath. The tube was irradiated for 35 hours by a 100 watt mercury vapor lamp which was situated in a large test tube and placed in the same bath 5-10 cm. from the reaction tube. Solvent was stripped off at reduced pressure on a rotary evaporator. Recrystallization of the solid product from cyclohexane gave 11.4 g of 2-(4-t-butylphenylsulfonyl)ethyltrimethylstannane, m.p. 118°-120°C. The presence of both the sulfonyl and trimethyltin groups was indicated by the strong infrared absorption bands at 1310 cm-1, 1262 cm-1, 1145 cm-1 (--SO2 --) and 770 cm-1 ((CH3)3Sn) using a KBr disc. Nuclear magnetic resonance spectroscopy (NMR) showed the following:

Workup

  1. additionAn 80 ml, two-necked, pyrex glass Schlenk reaction tube containing a Teflon coated magnetic stir bar
  2. temperaturemaintained in an air-free condition
  3. customplaced in a 20°C
  4. customwas situated in a large test tube
  5. customSolvent was stripped off at reduced pressure on a rotary evaporator
  6. customRecrystallization of the solid product from cyclohexane

Sources & evidence

ORD record
ord-0e9a15c1c08647a09b3c1d4d98adf4b8
Source dataset
uspto-grants-1976_08
Patent number
US03976672

Reaction notes

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