Sodium Hydroxide → HCID 58066392, compound

HRID 2410533Notes

Reaction equation

HRID 2410533 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18]C)=[O:17])=[CH:12][C:11]=2[CH2:20][O:21][CH3:22])[CH:9]=1>CCO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][C:11]=2[CH2:20][O:21][CH3:22])[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66678157HCID 66678157, compound

Product 1

HCID 58066392HCID 58066392, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A 5N aqueous solution of NaOH (3 mL, 15 mmol) was added into a solution of methyl 5′-fluoro-2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylate (2.88 g, 10.0 mmol) in EtOH (30 mL) and stirred at 60° C. for 1 hour. The reaction mixture was concentrated under vacuum. The residue was taken up with MTBE (100 mL), water (50 mL) and a 5N aqueous solution of HCl (4 mL). The layers were separated. The organic layer was washed with water (50 mL) and brine (50 mL). The aqueous layers were extracted with MTBE (50 mL). The organic layers were combined, dried (MgSO4) and concentrated under vacuum. After purification by crystallization from a mixture of MTBE and heptane, the title compound was obtained as a white powder (2.31 g, 84%). HPLC (Method A) Rt 3.9 min (Purity: 100%). LC/MS (Method B): 273.1 (M−H)−. 1H NMR (DMSO-d6, 300 MHz) δ 13.05 (s, 1H), 8.09 (d, J=1.7 Hz, 1H), 7.92 (dd, J=7.9, 1.7 Hz, 1H), 7.36 (dd, J=8.5, 6.0 Hz, 1H), 7.26 (d, J=7.9 Hz, 1H), 7.16 (m, 1H), 6.98 (dd, J=9.5, 2.8 Hz, 1H), 4.16 (d, J=12.5 Hz, 1H), 4.10 (d, J=12.5 Hz, 1H), 3.19 (s, 3H), 1.95 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe layers were separated
  3. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  4. extractionThe aqueous layers were extracted with MTBE (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customAfter purification
  8. customby crystallization
  9. additionfrom a mixture of MTBE and heptane

Sources & evidence

ORD record
ord-aee1a72b7564469aa19bca9c7fae97fd
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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