[3-(benzyloxy)-1,2-oxazol-5-yl]Methanol

[3-(benzyloxy)-1,2-oxazol-5-yl]Methanol Property

Boiling point:

396.6±32.0 °C(Predicted)

Density 

1.251±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

13.12±0.10(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

[3-(benzyloxy)-1,2-oxazol-5-yl]Methanol Chemical Properties,Usage,Production

Uses

(3-(Benzyloxy)isoxazol-5-yl)methanol is a key precursor to tetracycline antibiotics.

Synthesis

General procedure for the synthesis of (3-(benzyloxy)isoxazol-5-yl)methanol from methyl 3-(benzyloxy)isoxazole-5-carboxylate: to a solution of methyl 3-(benzyloxy)isoxazole-5-carboxylate (2.33 g, 9.99 mmol, 1.00 eq.) in methanol (50 mL) was added sodium borohydride (756 mg, 19.98 mmol, 2.00 equivalent). The reaction mixture was stirred at 15 °C for 3 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio of petroleum ether:ethyl acetate = 5:1) to confirm the completion of the reaction. The reaction mixture was slowly poured into 0.2 M hydrochloric acid solution (200 mL) and extracted with ethyl acetate (150 mL x 2). The organic phases were combined, washed with saturated saline (200 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give (3-(benzyloxy)isoxazol-5-yl)methanol (1.85 g, 9.02 mmol, 90% yield) as a colorless oil.LC-MS (ESI) m/z: 206.1 [M+H]+.

References

[1] Patent: WO2018/140809, 2018, A1. Location in patent: Paragraph 00443; 00551; 00554; 00555
[2] European Journal of Organic Chemistry, 1998, # 3, p. 473 - 479
[3] Patent: WO2012/87833, 2012, A1. Location in patent: Page/Page column 133
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9133 - 9153
[5] Patent: WO2008/127361, 2008, A2. Location in patent: Page/Page column 89