Hydrochloric Acid → (3-(5-Methyloxazol-2-yl)phenyl)methanol

HRID 41602Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16](O)=[O:17])=[N:10][CH:9]=1.Cl>C1COCC1>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[C:15]([CH2:16][OH:17])[CH:19]=[CH:20][CH:21]=2)=[N:10][CH:9]=1

Participants

Conditions

Temperature: 35 °C

Procedure

To a stirred suspension of LiAlH4 (0.29 g, 7.41 mmol) in THF (12 mL) a solution of 3-(5-methyloxazol-2-yl)benzoic acid [628297-39-2] (1.21 g, 5.84 mmol) in THF (3 mL) was added dropwise at 25° C. (exothermic) and the mixture was stirred at 35° C. for 30 min. The mixture was poured into 1N aqueous HCl solution and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (0.88 g, 80%). [1H NMR (400 MHz, CHLOROFORM-d) ♀ ppm 8.00 (s, 1H), 7.87-7.93 (m, 1H), 7.42 (d, J=4.8 Hz, 2H), 6.82 (s, 1H), 4.75 (br. s., 2H), 2.39 (s, 3H); LCMS RtA=0.75, [M+H]+=190.1].

Workup

additionwas added dropwise at 25° C. (exothermic)
extractionextracted with ethyl acetate (2×)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane)

Sources & evidence

ORD record: ord-e2d8d9e0e46949438839ff1e8d4a8ce9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530648B2

Reaction notes

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