Potassium Hydroxide → HCID 18687828, compound

HRID 1873149Notes

Reaction equation

HRID 1873149 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:37])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]3[C:16]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]([O:34]C)=[O:33])=[CH:26][CH:25]=4)=[C:17]4[C:22](=[CH:23][C:14]=3[S:13][C:12]=2[CH:36]=1)[CH:21]=[CH:20][CH:19]=[CH:18]4>C1COCC1.CO.O>[C:32]([CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:16]2[C:15]3[C:11]4[CH:10]=[CH:9][C:8]([O:7][CH2:6][C:5]([OH:37])=[O:4])=[CH:36][C:12]=4[S:13][C:14]=3[CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[CH:21]3)=[CH:25][CH:26]=1)([OH:34])=[O:33]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 53800336HCID 53800336, compound

Product 1

HCID 18687828HCID 18687828, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 N Aqueous potassium hydroxide (8.0 mL, 8.0 mmol) was added to a stirred suspension of [11 -(4-methoxycarbonylmethoxy-phenyl)-benzo[b]naphtho[2,3-d ]thiophen-3-yloxy]-acetic acid methyl ester (0.750 g, 1.54 mmol) in THF (20 mL) and methanol (13 mL). Dissolution occurred. After 3 h at ambient temperature, the reaction mixture was diluted with water and extracted with ether (100 mL). The aqueous phase was acidified with 10% aqueous HCl and filtered. The solid was washed with water and triturated with pet. ether. The solid was dried in vacuo at 70° C. to provide a grey solid. This solid was recrystalized from acetic acid to provide the title compound as a white solid (0.502, 71%): mp 220-222° C.: NMR (DMSO-d6); δ12.8 (broad s, 2 H), 8.54 (s, 1 H), 8.02 (d, J=8 Hz, 1 H), 7.56-7.40 (m, 4 H), 7.31 (d, J=8 Hz, 2 H), 7.23 (d, J=8 Hz, 2 H), 6.73 (dd, J=9, 1 Hz, 1 H), 6.56 (d, J=9 Hz, 1 H), 4.85 (s, 2 H), 4.74 (s, 2 H), 1.97 (s, 2.49 H, 0.83 mol acetic acid); MS (FAB+): 459 (20%, M+H); Anal. Calc. for C26H18O6S.0.83CH3CO2 H: C, 65.46, H, 4.24, N, 0.00. Found: C, 64.47, H, 4.05, N, 0.03.

Workup

  1. dissolutionDissolution
  2. extractionextracted with ether (100 mL)
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. customtriturated with pet. ether
  6. customThe solid was dried in vacuo at 70° C.
  7. customto provide a grey solid
  8. customThis solid was recrystalized from acetic acid

Sources & evidence

ORD record
ord-6fc83c7f6d7146999882655e95c6e6d4
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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