Tributylstannane → trans-4-Difluoromethyl-4-trimethylsiloxy-1-tri-n-butylstannyl-1-octene

HRID 903670Notes

Reaction equation

[F:1][CH:2]([F:16])[C:3]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6].[CH2:17]([SnH:21]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20].N(C(C)(C)C#N)=NC(C)(C)C#N>>[F:16][CH:2]([F:1])[C:3]([O:11][Si:12]([CH3:15])([CH3:13])[CH3:14])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4]/[CH:5]=[CH:6]/[Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Reactant 3

HCID 5948Tributylstannane

HCID 6547Azobisisobutyronitrile

HCID 217647864-Difluoromethyl-4-trimethylsiloxy-1-octyne

Product 1

HCID 21587526trans-4-Difluoromethyl-4-trimethylsiloxy-1-tri-n-butylstannyl-1-octene

Procedure

A mixture of 13.0 g. of 4-difluoromethyl-4-trimethylsiloxy-1-octyne, 17.23 ml. of tri-n-butylstannane and 70 mg. of azobisisobutyronitrile is heated under nitrogen in an oil bath at 125°-135° C. for 2 hours. The reaction is cooled to room temperature and vacuum distilled through a short-path apparatus, giving, after a 5 ml. forerun, 25.6 g. of the product as an oil, containing a minor amount of the corresponding cis isomer.

Workup

additionA mixture of 13.0 g
distillationvacuum distilled through a short-path apparatus
customgiving

Sources & evidence

ORD record: ord-5e8c825edd6c4e0ab88cc2e729248352
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04228298

Reaction notes

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