4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one Chemical Properties

Boiling point:

214℃

Density 

1.367

Flash point:

93℃

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

liquid

pka

14.54±0.10(Predicted)

color 

Pale yellow

InChI

InChI=1S/C5H6O4/c1-3-4(2-6)9-5(7)8-3/h6H,2H2,1H3

InChIKey

JEQSUJXHFAXJOW-UHFFFAOYSA-N

SMILES

O1C(C)=C(CO)OC1=O

Safety Information

HS Code 

2932990090

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one Usage And Synthesis

Description

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one is a reagent used in organic synthesis, particularly for the introduction of the non-chiral (oxodioxolenyl)methyl carbamate group to active pharmaceutical ingredients (APIs) to afford the corresponding pro-drug.

Definition

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one can be reacted with oxalyl chloride to afford (5-methyl-2-oxo-1,3-dioxol-4-yl) methylglyoxal chloride, which provides for an alternative approach to introduce the (oxodioxolenyl) methylcarbamate group.

Uses

4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one is used in preparation method of key intermediate of olmesartan medoxomil.

Preparation

At 20-25°C, 50 g of 4-chloromethyl-5-methyl-1,3-dioxol-2-one and 45 g of formic acid were added to 500 mL of acetonitrile. The reaction was cooled to 10-15°C followed by 95 g of triethylamine added. The mixture was heated to 60-65°C and stirred for approximately 5-6 h. The reaction system was subsequently cooled to 15-20°C, filtered, and washed with acetonitrile. Collecting filtrate, and the acetonitrile was removed under vacuum to concentrate the solution. The reaction system was again cooled to 25-30°C, and ethyl acetate and water were added. The mixture was then stirred for approximately 15-20 minutes at 25-30°C. Finally, 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one was obtained after further purification.

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