Ethylene Oxide → 1-Octyn-4-ol, 4-methyl-

HRID 1439801Notes

Reaction equation

[CH2:1]([C:5]1([CH3:8])[CH2:7][O:6]1)[CH2:2][CH2:3][CH3:4].[CH2:9]([Li])[CH2:10]CC.[H-].[Na+].O1CC1.[C-]#[C-].[Li+].[Li+].C(N)CN>>[CH3:8][C:5]([OH:6])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:7][C:9]#[CH:10]

Participants

Reactant 5

HCID 6354Ethylene Oxide

HCID 24758Sodium hydride

HCID 109204802-methyl-1,2-epoxyhexane

HCID 178418339Butyllithium

HCID 178511344HCID 178511344, compound

Product 1

HCID 109096581-Octyn-4-ol, 4-methyl-

Procedure

A fourth alternative procedure is typified by the formation of the 2-butyl-2-methyloxirane with n-butyl lithium or sodium hydride and reaction of this oxirane with lithium acetylide-ethylenediamine to directly produce the 4-methyl-1-octyn-4-ol as shown by reaction procedure (IIIb) of Scheme (I).

Sources & evidence

ORD record: ord-35c8a1f340834726b6f5a1b0ba3e7845
Source dataset: uspto-grants-1977_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04060691

Reaction notes

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