Sodium Hydroxide → HCID 58083444, compound

HRID 1630998Notes

Reaction equation

[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:25])([F:24])[F:23])[CH3:4]>CCO>[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:23])([F:24])[F:25])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A 5N aqueous solution of NaOH (4.1 mL, 20.5 mmol) was added into a solution of methyl 2-ethoxy-2′-(trifluoromethyl)biphenyl-4-carboxylate (4.45 g, 13.7 mmol) in EtOH (45 mL). The reaction mixture was heated at 60° C. for 30 minutes, and then concentrated under reduced pressure. The residue was taken up with water (50 mL) and a 5N aqueous solution of HCl (7 ml), and then extracted with MTBE (2×100 mL). The organic layers were washed with brine (50 mL), dried (MgSO4) and concentrated under reduced pressure to give a colorless oil. After precipitation from pentane, the title compound was obtained as a white powder. HPLC (Method A), Rt: 4.3 min (purity: 99.7%). UPLC/MS, M−(ESI): 309.0. 1H NMR (DMSO-d6, 300 MHz) δ 13.08 (s, 1H), 7.81 (d, J=7.7 Hz, 1H), 7.70 (m, 1H), 7.64-7.54 (m, 3H), 7.33 (d, J=7.5 Hz, 1H), 7.24 (d, J=7.7 Hz, 1H), 4.04 (m, 2H), 1.12 (t, J=7.0 Hz, 3H).

Workup

concentrationconcentrated under reduced pressure
extractiona 5N aqueous solution of HCl (7 ml), and then extracted with MTBE (2×100 mL)
washThe organic layers were washed with brine (50 mL)
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
customto give a colorless oil
customAfter precipitation from pentane

Sources & evidence

ORD record: ord-8188e018403a406492f0e344a089dceb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791142B2

Reaction notes

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