Potassium Hydroxide → HCID 18430706, compound

HRID 1069239Notes

Reaction equation

HRID 1069239 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([O:24]C(=O)C)=[C:19]([CH3:28])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[OH-].[K+]>O1CCCC1.CO>[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([OH:24])=[C:19]([CH3:28])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10297816HCID 10297816, compound

Product 1

HCID 18430706HCID 18430706, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetic acid 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenyl ester (6.5 g, 14.3 mmol) in tetrahydrofuran (240 mL) and methanol (80 mL) at room temperature was added dropwise aqueous potassium hydroxide (17.2 mL of a 1N solution, 17.2 mmol). After 4 h at room temperature the reaction mixture was placed in the freezer for 18 h. The reaction was removed from the freezer and allowed to stir at room temperature. More aqueous potassium hydroxide (41.5 mL of a 1N solution, 41.5 mmol), tetrahydrofuran (50 mL), and methanol (10 mL) were added. The mixture was diluted with water (500 mL), acidified with 1N aqueous solution of hydrochloric acid, and extracted with diethyl ether. The diethyl ether layer was washed twice with water (500 mL), and dried (MgSO4). Concentration under reduced pressure gave a residue which was adsorbed onto silica gel. Chromatography with petroleum ether:ethyl acetate (97:3, then 95:5) gave the title compound as a white foamy solid (5.5 g, 93%): NMR (CDCl3): δ8.41 (s, 1H), 8.16 (d, 1H), 7.64-7.54 (m, 2H), 7.46-7.40 (m, 1H), 6.89 (s, 2H), 2.41 (s, 3H), 2.23 (s, 6H), 1.60 (s, 3H); MS(−ESI): [M−H], 1 bromine isotope pattern, 409/411.

Workup

  1. customThe reaction was removed from the freezer
  2. additionMore aqueous potassium hydroxide (41.5 mL of a 1N solution, 41.5 mmol), tetrahydrofuran (50 mL), and methanol (10 mL) were added
  3. additionThe mixture was diluted with water (500 mL)
  4. extractionextracted with diethyl ether
  5. washThe diethyl ether layer was washed twice with water (500 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationConcentration under reduced pressure
  8. customgave a residue which

Sources & evidence

ORD record
ord-e13ff547ddbb401a966164e404fa7d64
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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