Sodium Hydroxide → HCID 68654585, compound

HRID 229251Notes

Reaction equation

HRID 229251 reaction equation
C([O:3][C:4](=[O:29])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[C:21]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[C:9]([F:28])[CH:8]=1)C.[OH-].[Na+]>C1COCC1.C(O)C>[C:21]1(=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:10]2[CH:11]=[CH:12][C:7]([CH:6]=[CH:5][C:4]([OH:29])=[O:3])=[CH:8][C:9]=2[F:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68654609HCID 68654609, compound

Product 1

HCID 68654585HCID 68654585, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-{4-[cycloheptylidene-(4-hydroxy-phenyl)-methyl]-3-fluoro-phenyl}acrylic acid ethyl ester (176) (0.8 g, 2.15 mmol) in THF (10 mL) and ethanol (10 mL) was added 1 N sodium hydroxide (21 mL). The reaction mixture was heated at 65° C. for 2.5 h. The reaction mixture was partially concentrated to remove the EtOH and THF. To the basic aqueous mixture was added 1 N HCl to pH˜1 (according to litmus paper). The acidic aqueous solution was extracted with dichloromethane and the organic extract was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was triturated with dichloromethane, filtered and dried to give 0.065 g (10%) of compound 177 as a white powder. 1H NMR (400 MHz, DMSO-d6): δ 1.51 (b, 8H), 2.09 (m, 2H), 2.25 (m, 2H), 6.52 (d, J=16.1 Hz, 1H), 6.65 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 7.19 (t, J=7.8 Hz, 1H), 7.43-7.49 (m, 1H), 7.51-7.53 (m, 2H), 9.32 (s, 1H), 12.43 (s, 1H). HRMS (ESI) Calcd for C23H22FO3: 365.1553 (M−H)−. Found: 365.1543.

Workup

  1. concentrationThe reaction mixture was partially concentrated
  2. customto remove the EtOH and THF
  3. additionTo the basic aqueous mixture was added 1 N HCl to pH˜1 (according to litmus paper)
  4. extractionThe acidic aqueous solution was extracted with dichloromethane
  5. extractionthe organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was triturated with dichloromethane
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-10412e86a30b48a298a83e6fbf61c820
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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