Tributylstannane → E-1-Tri-n-butylstannyl-4-methyl-4-tri-methylsilyloxy-7-oxa-1-octene

HRID 848911Notes

Reaction equation

HRID 848911 reaction equation
[CH3:1][C:2]([O:10][Si:11]([CH3:14])([CH3:13])[CH3:12])([CH2:6][CH2:7][O:8][CH3:9])[CH2:3][C:4]#[CH:5].N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:27]([SnH:31]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]>>[CH2:36]([Sn:31]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:32][CH2:33][CH2:34][CH3:35])/[CH:5]=[CH:4]/[CH2:3][C:2]([CH3:1])([O:10][Si:11]([CH3:14])([CH3:12])[CH3:13])[CH2:6][CH2:7][O:8][CH3:9])[CH2:37][CH2:38][CH3:39]

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 127862304-Methyl-4-trimethylsilyloxy-7-oxa-1octyne

Product 1

HCID 12786231E-1-Tri-n-butylstannyl-4-methyl-4-tri-methylsilyloxy-7-oxa-1-octene

Procedure

To a stirred solution of 15 g. (0.069 moles) of 4-methyl-4-trimethylsilyloxy-7-oxa-1octyne and 75 mg. of azobisisobutyronitrile is added dropwise, under nitrogen atmosphere, 21.1 g. (0.073 moles) of tri-n-butyltin hydride. The solution is stirred at 130°-135° C. for 11/2 hours, then cooled to ambient temperature. Distillation provides 29 g. (86%) of product as a colorless oil; b.p. 165°-167° C. (0.25 mm.).

Workup

  1. distillationDistillation
  2. customprovides 29 g

Sources & evidence

ORD record
ord-1d20a628ce4f40c48c5c0f93c72ddc7e
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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