Tributylstannane → Tert-butyl-dimethyl-(4-tributylstannanyl-but-3-enyloxy)-silane

HRID 73308

Reaction equation

HRID 73308 reaction equation
[C:1]([Si:5]([O:8][CH2:9][CH2:10][C:11]#[CH:12])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([SnH:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[C:1]([Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH:11]=[CH:12][Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH3:16])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

Product 1

HCID 85142049Tert-butyl-dimethyl-(4-tributylstannanyl-but-3-enyloxy)-silaneYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of Example 31A (1.08 g, 5687 mmol), tri-(n-butyl)tin hydride (1.43 mL, 5.31 mmol), and AIBN (cat.) in benzene (10 mL) was stirred at 80° C. for 3 hours. Volatiles were removed under reduced pressure to provide the title compound as a colorless oil (>95% E-isomer). 1H NMR (300 MHz, CDCl3): δ 0.05 (s, 6H), 0.80-0.98 (m, 15H), 0.90 (s, 9H), 1.23-1.38 (m, 6H), 1.42-1.53 (m, 6H), 2.34-2.40 (m, 2H), 3.66 (d, J=6 Hz, 2H), 5.94-5.98 (m, 2H).

Workup

  1. customVolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-25012324cdb343cab96c1dd75ae95dc2
Source dataset
uspto-grants-2014_09
Patent number
US08829041B2

Linked notes

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