Trifluoroacetic acid → methyl 4-[1-hydroxy-1-(1H-pyrazol-4-yl)ethyl]benzoate

HRID 595299Notes

Reaction equation

C(O)(C(F)(F)F)=O.[OH:8][C:9]([C:35]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=1)([C:11]1[CH:12]=[N:13][N:14](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:15]=1)[CH3:10].C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:8][C:9]([C:35]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=1)([C:11]1[CH:12]=[N:13][NH:14][CH:15]=1)[CH3:10]

Participants

Conditions

Temperature: -40 °C

Procedure

TFA (0.1 mL) in DCM (2 mL) were added dropwise to a mixture of methyl 4-[1-hydroxy-1-(1-trityl-1H-pyrazol-4-yl)ethyl]benzoate (0.2 g, 0.8 mmol), triethylsilane (0.2 mL) in DCM (5 mL) cooled to −40° C. Then the mixture was stirred at −40° C. for 2 hours. The mixture was adjusted to pH 7 by adding aqueous sodium bicarbonate solution at −40° C. After the reaction warmed to room temperature, the mixture was extracted with ethyl acetate. The organic layer was concentrated and the residue was purified by preparative thin layer chromatography to afford methyl 4-[1-hydroxy-1-(1H-pyrazol-4-yl)ethyl]benzoate. MS ESI calc'd. for C13H15N2O3 [M+H]+ 247. found 247. 1H NMR (400 MHz, CD3OD): δ 7.98 (d, J=8.4 Hz, 2H), 7.59 (d, J=8.4 Hz, 2H), 7.50 (s, 2H), 3.90 (s, 3H), 1.89 (s, 3H).

Workup

temperatureAfter the reaction warmed to room temperature
extractionthe mixture was extracted with ethyl acetate
concentrationThe organic layer was concentrated
customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-b2aadfdb12904a07847a55ae50dc139f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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