Triethylamine → HCID 59627642, compound

HRID 1930146Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][C:18]=1[CH3:28].C(N(CC)CC)C>C(Cl)Cl.O>[CH3:28][C:18]1[CH:19]=[C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:22][C:17]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Participants

Conditions

Temperature: 18 °C

Procedure

Trifluoromethane sulfonic anhydride (0.217 mL, 1.32 mmol) was added dropwise to methyl 2-(4-hydroxy-3-methylphenyl)acetate (159 mg, 0.88 mmol), in DCM (4 mL) at 0° C. under nitrogen. The resulting solution was then treated with triethylamine (0.369 mL, 2.65 mmol) and allowed to warm to and stir at 18° C. for 16 hours. The mixture was diluted with DCM (20 mL) and water (20 mL) and the organics separated. The organics were washed with saturated NaHCO3 (aq, 50 mL), brine (10 mL) dried (MgSO4) and evaporated to crude material. The crude product was purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 2-(3-methyl-4-(trifluoromethylsulfonyloxy)phenyl)acetate (169 mg, 61.3%) as a colourless oil.

Workup

temperatureto warm to and
washThe organics were washed with saturated NaHCO3 (aq, 50 mL), brine (10 mL)
dry with materialdried (MgSO4)
customevaporated to crude material
customThe crude product was purified by flash silica chromatography, elution gradient 0 to 30% EtOAc in isohexane
customPure fractions were evaporated to dryness

Sources & evidence

ORD record: ord-c598264eb6fc4bf7901ee94b4c9422d9
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188092B2

Reaction notes

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