Tributylstannane → HCID 13168697, compound

HRID 1604055Notes

Reaction equation

[CH3:1][O:2]/[CH:3]=[CH:4]/[C:5]#[CH:6].[CH2:7]([SnH:11]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH3:10].N(C(C)(C)C#N)=NC(C)(C)C#N>>[CH2:16]([Sn:11]([CH2:7][CH2:8][CH2:9][CH3:10])([CH2:12][CH2:13][CH2:14][CH3:15])/[CH:6]=[CH:5]/[CH:4]=[CH:3]/[O:2][CH3:1])[CH2:17][CH2:18][CH3:19]

Participants

Reactant 3

HCID 5948Tributylstannane

HCID 6547Azobisisobutyronitrile

HCID 6431882798-73-4

Product 1

HCID 13168697HCID 13168697, compound

Procedure

Scheme D shows a method of preparing an aldehyde which may be used in Scheme A. 1-Methoxy-1E-buten-3-yne is reacted with tributylstannane in the presence of catylytic 2,2'-azobisisobutyronitrile (AIBN) to give tributyl(4-methoxy-1E,3E-butadienyl)stannane which is then reacted with butyllithium followed by coupling with an appropriate aldehyde (XVIII). The alcohol-formed is reacted with toluene sulfonic acid (TSOH) to give the desired aldehyde (V).

Sources & evidence

ORD record: ord-ea0d9129f3764ca49791278c110764c1
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990326

Reaction notes

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