Iodine → 1-Iodo-3-methoxy-trans-1-octene

Reaction equation

[CH3:1][O:2][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:4]#[CH:5].C(BC(C(C)C)C)(C(C)C)C.C[N+]([O-])(C)C.[OH-].[Na+].[I:29]I>>[I:29]/[CH:5]=[CH:4]/[CH:3]([O:2][CH3:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Reactant 5

HCID 807Iodine

HCID 1145Trimethylamine oxide

HCID 14798Sodium Hydroxide

HCID 192733Bis(1,2-dimethylpropyl)borane

HCID 146912763-Methoxyoct-1-yne

Product 1

HCID 204656481-Iodo-3-methoxy-trans-1-octene

Procedure

Treatment of 3-methoxy-1-octyne (Example 1877) with disiamylborane, trimethylamine oxide, sodium hydroxide and iodine by the procedure described in Example 996 furnishes the title product.

Sources & evidence

ORD record: ord-52cc04caf3754467ad32d579799bc673
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04007210

Reaction notes

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