tert-Butyl ethyl ethanedioate → HCID 21535782, compound

HRID 1077053Notes

Reaction equation

HRID 1077053 reaction equation
[Li][C:2]#[C:3][CH:4]([CH3:6])[CH3:5].[C:7](OCC)(=[O:15])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>C1COCC1>[CH3:5][CH:4]([CH3:6])[C:3]#[C:2][C:7](=[O:15])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 14648212tert-Butyl ethyl ethanedioateHCID 178506794HCID 178506794, compound2×

Product 1

HCID 21535782HCID 21535782, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

reacting 1-lithio-3-methylbut-1-yne with a 150% to 165% excess of the stoichiometric amount of ethyl t-butyl oxalate in THF containing an amount of a suitable hydrocarbon solvent sufficient to solubilize said 1-lithio-3-methylbut-1-yne, the reaction being carried out under anhydrous conditions in an inert atmosphere at a temperature of from 0° to 10° to form t-butyl 5-methyl-2-oxohex-3-ynoate;

Workup

  1. custombeing carried out under anhydrous conditions in an inert atmosphere at a temperature of from 0° to 10°

Sources & evidence

ORD record
ord-918ae0e292d846618cd235d7a51b64e5
Source dataset
uspto-grants-1976_05
Patent number
US03959312

Reaction notes

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