2,2-Dimethyl-5-(hydroxymethyl)-1,3-dixoane Chemical Properties

Melting point:

197-198℃

Boiling point:

208℃

Density 

1.004

Flash point:

96℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

14.58±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C7H14O3/c1-7(2)9-4-6(3-8)5-10-7/h6,8H,3-5H2,1-2H3

InChIKey

BTAUZIVCHJIXAX-UHFFFAOYSA-N

SMILES

O1CC(CO)COC1(C)C

2,2-Dimethyl-5-(hydroxymethyl)-1,3-dixoane Usage And Synthesis

Synthesis

Example 25 Synthesis of 1-(3-(3-hydroxy-2-(hydroxymethyl)propoxy)-4-methyl-1-phenyl-1H-pyrazol-5-yl)-3-(2-phenyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)urea Step A: Preparation of (2,2-dimethyl-1,3-dioxan-5-yl)methanol: To a suspension of 2-hydroxymethyl-1,3-propanediol (5.0 g, 47.1 mmol) in THF (100 mL) was added p-toluenesulfonic acid (pTsOH, 269 mg, 1.41 mmol), followed by 2,2-dimethoxypropane (6.72 mL. 54.7 mmol). The reaction mixture was stirred at room temperature for 3 hours, then p-toluenesulfonic acid (200 mg) was added and stirring was continued at room temperature for 48 hours. Upon completion of the reaction, triethylamine (3 mL) was added to neutralize the reaction system and the mixture was subsequently concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% methanol/dichloromethane as eluent to afford (2,2-dimethyl-1,3-dioxan-5-yl) methanol (5.04 g, 73% yield) as a colorless liquid.1H NMR (CDCl3) δ 4.02 (dd, J = 12.0, 4.1 Hz, 2H), 3.74-3.80 (m, 4H), and 1.90 (t, J = 5.1 Hz, 1H), 1.78-1.88 (m, 1H), 1.45 (s, 3H), 1.40 (s, 3H) ppm.

References

[1] Journal of Medicinal Chemistry, 2002, vol. 45, # 26, p. 5694 - 5709
[2] Patent: WO2008/157726, 2008, A1. Location in patent: Page/Page column 210
[3] Patent: EP2103611, 2009, A1. Location in patent: Page/Page column 51-52
[4] Patent: WO2008/124703, 2008, A2. Location in patent: Page/Page column 84
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 187 - 196

2,2-Dimethyl-5-(hydroxymethyl)-1,3-dixoane(4728-12-5)Related Product Information

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