Sodium Hydroxide → HCID 22323765, compound

HRID 1955537Notes

Reaction equation

HRID 1955537 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][C:14](C)=[C:15]([CH3:17])[N:16]=2)[C:8]2[CH:7]=[C:6]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+]>CCO>[CH3:1][C:2]1([CH3:32])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[C:15]([CH3:17])[N:16]=2)[C:8]2[CH:7]=[C:6]([C:19]#[C:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22323785HCID 22323785, compound2×

Product 1

HCID 22323765HCID 22323765, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 4-[5,6-dihydro-5,5-dimethyl-8-(4,5-dimethylthiazol-2-yl)-2-naphthalenyl]ethynylbenzoate (Compound 17) (58.0 mg, 0.13 mmol) and 4 ml of EtOH at room temperature was added aqueous NaOH (1 ml, 1M, 1 mmol). The resulting solution was warmed to 50° C. for 1 hour and concentrated in vacuo. The residue was suspended in a solution of CH2Cl2 and ether (5:1) and acidified to pH 5 with 1M aqueous HCl. The layers were separated and the organic layer was washed with brine, dried (Na2O4), filtered and the solvents removed under reduced pressure to give the title compound as a white solid. 1H NMR (d6-DMSO): δ 7.94 (2H, d, J=8.4 Hz), 7.86 (1H, d, J=1.6 Hz), 7.61 (2H, d, J=8.3 Hz), 7.50 (1H, dd, J=1.6, 8.0 Hz), 7.45 (1H, d, J=8.0 Hz), 6.51 (1H, t, J=4.9 Hz), 2.37 (3H, s), 2.36 (2H, d, J=4.6 Hz), 2.32 (3H, s), 1.26 (6H, s).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. customdried (Na2O4)
  5. filtrationfiltered
  6. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-68473db659f64aed9fa836e5c9249c39
Source dataset
uspto-grants-1998_07
Patent number
US05776699

Reaction notes

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