Trimethylstannane → 11-(p-Tolylsulfonyl)undecyltrimethylstannane

HRID 1283863Notes

Reaction equation

HRID 1283863 reaction equation
[CH2:1]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[CH3:22][SnH:23]([CH3:25])[CH3:24]>>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([S:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Sn:23]([CH3:25])([CH3:24])[CH3:22])(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 12623Trimethylstannane2×HCID 2147553210-Undecenyl-p-tolyl sulfone

Product 1

HCID 2346663411-(p-Tolylsulfonyl)undecyltrimethylstannane

Procedure

The procedure described in Example 1 was employed except that 13.1 g (42.5 mmoles) of 10-undecenyl-p-tolyl sulfone and 14.0 g (85 mmoles) of trimethyltin hydride were the reactants. The reaction mixture was irradiated for 189 hours. The excess trimethyltin hydride was allowed to evaporate from the reaction mixture under a flow of nitrogen. The residual oil weighed 15.5 g. One-half of the crude product was chromatographed on a column containing silica gel using toluene and 2% acetone in toluene as eluents. The product, 11-(p-tolylsulfonyl)-undecyltrimethylstannane, was obtained as an oil. The presence of both the sulfonyl and trimethyltin groups was indicated by the strong infrared absorption bands at 1315 cm-1, 1300 cm-1, 1285 cm-1, 1140 cm-1 (--SO2 ) and 760 cm-1 [(CH3)3Sn--]. NMR showed the following:

Workup

  1. customThe reaction mixture was irradiated for 189 hours
  2. customto evaporate from the reaction mixture under a flow of nitrogen
  3. customOne-half of the crude product was chromatographed on a column
  4. additioncontaining silica gel

Sources & evidence

ORD record
ord-54c802d2ee604062837dc11c63523a24
Source dataset
uspto-grants-1976_08
Patent number
US03976672

Reaction notes

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