Boron trifluoride etherate → HCID 68278578, compound

HRID 931525Notes

Reaction equation

B(F)(F)F.CCOCC.[BH4-].[Na+].[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:23][C:24]([CH3:32])=[C:25]([CH2:27][CH2:28][C:29](O)=[O:30])[N:26]=2)=[CH:18][CH:17]=1)=[O:15]>O1CCCC1>[OH:30][CH2:29][CH2:28][CH2:27][C:25]1[N:26]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:21][CH:20]=2)[O:23][C:24]=1[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

Boron trifluoride etherate (4 g) was added dropwise with stirring to a mixture of sodium borohydride (720 mg, 19.03 mmol, 2.02 equiv) in tetrahydrofuran (35 mL) maintained under nitrogen at 0° C. The resulting solution was warmed to room temperature and stirred for 2 h. The above mixture was cooled to 0° C. then 3-[2-[4-(methoxycarbonyl)phenyl]-5-methyl-1,3-oxazol-4-yl]propanoic acid (2.72 g, 9.40 mmol, 1.00 equiv) was added in several batches. The reaction mixture was stirring at room temperature overnight and then quenched with 5 mL of methanol and 60 mL of water. The resulting solution was extracted with 50 mL of ethyl acetate. The organic layer was dried over anhydrous calcium chloride and concentrated under vacuum to give 2.2 g (85%) of methyl 4-[4-(3-hydroxypropyl)-5-methyl-1,3-oxazol-2-yl]benzoate as a white solid. LC-MS: (ES, m/z): 276 [M+H]+, 146, 115.

Workup

temperatureThe resulting solution was warmed to room temperature
temperatureThe above mixture was cooled to 0° C.
stirringThe reaction mixture was stirring at room temperature overnight
customquenched with 5 mL of methanol and 60 mL of water
extractionThe resulting solution was extracted with 50 mL of ethyl acetate
dry with materialThe organic layer was dried over anhydrous calcium chloride
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-de768ee841d8402db061d15fe79b5af8
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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