1,3-Diacetoxyacetone → 2-[(Acetyloxy)methyl]-2-hydroxybut-3-yn-1-yl acetate

HRID 417889Notes

Reaction equation

HRID 417889 reaction equation
[C:1]([Mg]Br)#[CH:2].[C:5]([O:8][CH2:9][C:10]([CH2:12][O:13][C:14](=[O:16])[CH3:15])=[O:11])(=[O:7])[CH3:6]>C1COCC1>[C:14]([O:13][CH2:12][C:10]([C:1]#[CH:2])([OH:11])[CH2:9][O:8][C:5](=[O:7])[CH3:6])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 2434181,3-DiacetoxyacetoneHCID 178418486HCID 178418486, compound

Product 1

HCID 598421902-[(Acetyloxy)methyl]-2-hydroxybut-3-yn-1-yl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

An ethynylmagnesium bromide solution (0.5 M in THF) was cooled to −78° C. under nitrogen. A solution of 1,3-diacetoxyacetone (0.5 g) in THF (3.0 mL) was added, and the resulting mixture was stirred for 30 min at −78° C., then at 0° C. for 5 min, quenched with 1.0 N aq. HCl (3 mL) and extracted in EtOAc. Evaporation gave crude 2-ethynyl-2-hydroxypropane-1,3-diyl diacetate, contaminated with about 50 mol % of 1,3-dacetoxyacetone. The crude material was used without further purification.

Workup

  1. waitat 0° C. for 5 min
  2. customquenched with 1.0 N aq. HCl (3 mL)
  3. extractionextracted in EtOAc
  4. customEvaporation

Sources & evidence

ORD record
ord-eda0931498d64be69f8cbb9c7b7f5ad5
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

Loading…