Methanol → 5-(3-Hydroxymethyl-phenyl)-oxazole-4-carboxylic acid methyl ester

HRID 42789Notes

Reaction equation

N#N.[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18](O)=[O:19])[CH:13]=1)=[O:6].CO>C1COCC1>[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][OH:19])[CH:13]=1)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 5-(3-carboxy-phenyl)-oxazole-4-carboxylic acid methyl ester (500 mg, 2.02 mmol) in THF (14.0 mL) at 0° C. was treated dropwise with BH3 (10.1 mL of a 1M solution in THF, 10.11 mmol). The resulting mixture was stirred at 0° C. for 4 h. MeOH (14 mL) was then added dropwise. After 30 min, the solvent was removed under reduced pressure. EA (20 mL) was added and the organic phase was washed with 1N NaOH (10 mL), water (10 mL) and brine (10 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (93:7 CH2Cl2-MeOH) gave the title compound as a white solid. TLC:rf (93:7 CH2Cl2-MeOH)=0.32. LC-MS-conditions 02: tR=0.76 min, [M+H]+=234.39.

Workup

waitAfter 30 min
customthe solvent was removed under reduced pressure
additionEA (20 mL) was added
washthe organic phase was washed with 1N NaOH (10 mL), water (10 mL) and brine (10 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customthe solvent removed under reduced pressure
customPurification of the residue by FC (93:7 CH2Cl2-MeOH)

Sources & evidence

ORD record: ord-c64aa5274f094c10b6e3379ab59b16b7
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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