Hydrochloric Acid → HCID 68534631, compound

HRID 1992815Notes

Reaction equation

HRID 1992815 reaction equation
[CH3:1][C:2]1[C:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25]CC)=[O:24])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][C:2]1[C:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86616636HCID 86616636, compound

Product 1

HCID 68534631HCID 68534631, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl (2E)-3-(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoate (9) (2.20 g, 5.02 mmol) was dissolved in THF and EtOH (1:1, 50 mL). To this mixture was added 1 N NaOH (50 mL, excess) at room temperature and the stirred reaction heated to 70° C. for 0.5 h. After cooling to RT, 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 CHCl3:MeOH (9:1 to 4:1) as an eluent to give 2.02 g (98%) of compound (10) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.70 (d, J=8.0 Hz, 1H), 7.64 (d, J=16.0 Hz, 1H), 7.57 (s, 1H), 7.26 (dd, J1=12.0 Hz, J2=12.0 Hz, 4H), 7.22 (d, J=4.0 Hz, 1H), 7.14 (d, J=1.8 Hz, 2H), 7.12 (s, 1H), 7.06 and 7.04 (dd, J=12.0 Hz, J2=6.8 Hz, 1H), 6.60 (d, J=8.0 Hz, 2H), 6.22 (d, J=16.0 Hz, 1H), 3.92 (s, 3H), 2.24 (s, 3H). LCMS (ESI) m/z 439.07 (M+H)+.

Workup

  1. customthe stirred reaction
  2. temperatureAfter cooling to RT
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customThe product was purified by flash column chromatography with CHCl3:MeOH (9:1 to 4:1) as an eluent

Sources & evidence

ORD record
ord-edf5b5aab98545979eba87d92852019b
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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