(2S)-1,4-Dioxan-2-yl-methanol Chemical Properties

Boiling point:

208.2±15.0 °C(Predicted)

Density 

1.102

storage temp. 

2-8°C

pka

14.24±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C5H10O3/c6-3-5-4-7-1-2-8-5/h5-6H,1-4H2/t5-/m0/s1

InChIKey

CMEPUAROFJSGJN-YFKPBYRVSA-N

SMILES

O1CCOC[C@@H]1CO

Safety Information

RIDADR 

UN1993

(2S)-1,4-Dioxan-2-yl-methanol Usage And Synthesis

Synthesis

General procedure for the synthesis of (S)-(1,4-dioxan-2-yl)methanol from the compound (CAS: 917882-63-4): palladium carbon (10% w/w, 192 mg) was added to an ethanol solution (20 mL) of intermediate 83 (1.25 g, 4.74 mmol). The reaction mixture was stirred under hydrogen atmosphere for 18 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filter cake was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to give 600 mg of the target product in 89% yield. The product was characterized by 1H NMR (500 MHz, Chloroform-d) with chemical shifts δ (ppm): 3.85-3.67 (m, 5H), 3.66-3.57 (m, 2H), 3.55 (dd, J = 11.7, 5.9 Hz, 1H), 3.46 (dd, J = 11.1, 10.0 Hz, 1H), 1.75 (s, 1H).

References

[1] Patent: WO2016/91776, 2016, A1. Location in patent: Page/Page column 233
[2] Patent: US2006/293358, 2006, A1. Location in patent: Page/Page column 50
[3] Patent: US2009/182002, 2009, A1. Location in patent: Page/Page column 15
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 12, p. 4092 - 4108