Diazomethane → Methyl 2,2-dimethylbut-3-ynoate

HRID 468364Notes

Reaction equation

HRID 468364 reaction equation
[N+](=[CH2:3])=[N-].[CH3:4][C:5]([CH3:11])([C:9]#[CH:10])[C:6]([OH:8])=[O:7]>CCOCC>[CH3:4][C:5]([CH3:11])([C:9]#[CH:10])[C:6]([O:8][CH3:3])=[O:7]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 139056472,2-Dimethylbut-3-ynoic acid

Product 1

HCID 15186997Methyl 2,2-dimethylbut-3-ynoateYield 46.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of diazomethane (−10 g) in ether (400 mL) was added dropwise 2,2-dimethyl-but-3-ynoic acid (10.5 g, 93.7 mmol) at 0° C. The mixture was warmed to room temperature and stirred overnight. The mixture was distilled under atmospheric pressure to give crude methyl 2,2-dimethylbut-3-ynoate (14 g), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 3.76 (s, 3H), 2.28 (s, 1H), 1.50 (s, 6H).

Workup

  1. distillationThe mixture was distilled under atmospheric pressure

Sources & evidence

ORD record
ord-901f826060714315bb9eb5c8939fa03e
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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