3-Butyn-2-ol → Methyl [(1-methyl-2-propynyl)oxy]acetate

HRID 1837096Notes

Reaction equation

[H-].[Na+].[CH3:3][CH:4]([OH:7])[C:5]#[CH:6].Br[CH2:9][C:10]([O:12][CH3:13])=[O:11]>>[CH3:3][CH:4]([O:7][CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]#[CH:6]

Participants

Reactant 3

HCID 162393-Butyn-2-ol

HCID 24758Sodium hydride

HCID 60984Methyl bromoacetate

Product 1

HCID 18619750Methyl [(1-methyl-2-propynyl)oxy]acetate

Procedure

Sodium hydride (60% dispersion in mineral oil, 10 g, 0.25 mol), (±)-3-butyn-2-ol (21 g, 0.30 mol), and methyl bromoacetate were processed as described in Example 43A to provide the title compound. 1H NMR (CDCl3) δ 1.51 (d, 3H), 2.46 (d, 1H), 3.76 (s, 3H), 4.25 (AB q, 2H), 4.39 (dq, 1H).

Sources & evidence

ORD record: ord-ad9bda268a0a42f0ab708ff0d326f671
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780872B2

Reaction notes

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