Reaction #59874

Reaction equation

2-(hydroxymethyl)-1,3-propanediol

1,3-difluoroacetone

trimethyl orthoformate

p-toluenesulfonic acid monohydrate

→

title compound

Yield 43.4%

(2,2-bis(fluoromethyl)-1,3-dioxan-5-yl)methanol

Yield 43.4%

Solvents

triethylamine

Conditions

Workup

1. 1
   workup.ADDITIONwas added to the reaction mixture, which
2. 2
   Concentrationwas then concentrated
3. 3
   OtherThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Procedure

A mixture of 2-(hydroxymethyl)-1,3-propanediol (2.2 g, 20.7 mmol), 1,3-difluoroacetone (3.89 g, 41.4 mmol), trimethyl orthoformate (3.44 ml, 20.7 mmol), and p-toluenesulfonic acid monohydrate (356 mg, 2.07 mmol) was stirred at 60° C. for 10 hours. After completion of the reaction, triethylamine (577 μl) was added to the reaction mixture, which was then concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (1.6 g, yield: 43.4%) as a light yellow oil.

Source