Hydrochloric Acid → HCID 11452260, compound

HRID 2241029Notes

Reaction equation

HRID 2241029 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C1COCC1.CCO>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:13](=[C:14]2[CH2:15][C:16]([CH3:23])([CH3:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH2:19]2)[C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:31])=[O:3])=[CH:8][CH:9]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86646615HCID 86646615, compound

Product 1

HCID 11452260HCID 11452260, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of ethyl({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)acetate (10) (0.290 g, 0.68 mmol) in THF/EtOH (1:1, 8 mL) was treated with 1 N NaOH (4 mL) at 70° C. for 1 h. The reaction mixture was acidified with 20% aqueous HCl, and then extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by flash column chromatography with chloroform and methanol as an eluent to afford 0.250 g (95%) of the title compound 11 as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 7.19-7.14 (m, 2H), 7.13 (d, J=9.3 Hz, 2H), 7.07 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.7 Hz, 1H), 6.84 (d, J=8.7 Hz, 2H), 4.63 (s, 2H), 1.93 (s, 2H), 1.88 (s, 2H), 1.27 (s, 2H), 0.90 (s, 12H). LCMS (ESI): m/z 395 (M−H)−.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customThe product was purified by flash column chromatography with chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-fd3287a4a17747e89d530d48d73c9bac
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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