Trimethylstannane → 4-(4-t-Butylphenylsulfonyl)butyltrimethylstannane

HRID 1283861Notes

Reaction equation

[CH:1]([C:5]1[CH:6]=[C:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[C:20](C=CCC)[CH:19]=2)(=[O:17])=[O:16])C=CC=1C(C)(C)C)=CCC.[CH3:32][SnH:33]([CH3:35])[CH3:34]>>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([S:15]([CH2:7][CH2:6][CH2:5][CH2:1][Sn:33]([CH3:35])([CH3:34])[CH3:32])(=[O:17])=[O:16])=[CH:19][CH:20]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

Reactant 2

HCID 12623Trimethylstannane

HCID 705653763-Butenyl-4-t-butylphenyl sulfone

Product 1

HCID 234667754-(4-t-Butylphenylsulfonyl)butyltrimethylstannaneYield 20.3%

Procedure

The procedure described in Example 1 was employed except that 10.7 g (42.5 mmoles) of 3-butenyl-4-t-butylphenyl sulfone and 7.0 g (42.5 mmoles) of trimethyltin hydride were the reactants. The irradiation proceeded for 70 hours. Recrystallization of the product from petroleum ether afforded 3.6 g of 4-(p-t-butylphenyl-sulfonyl)butyltrimethylstannane, m.p. 80°-81.8° C. The presence of both the sulfonyl and trimethyltin moieties was indicated by strong infrared absorption bands at 1300 cm-1, 1282 cm-1, 1147 cm-1 (--SO2 --) and 780 cm-1 [(CH3)3Sn--] employing a KBR disc. Nuclear magnetic resonance spectroscopy (NMR) showed the following:

Workup

customThe irradiation
customRecrystallization of the product from petroleum ether

Sources & evidence

ORD record: ord-51c44279ec6341eeb945508f20206d61
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03976672

Reaction notes

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