Tetrahydrofuran → {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid

HRID 456842Notes

Reaction equation

HRID 456842 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]([O:32]C)=[O:31])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[C@H](NCCC1C=CC(O)=CC=1)[C@H](O)C1C=CC(O)=CC=1.[OH-].[Na+].C1COCC1>O.CO>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]([OH:32])=[O:31])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 33572RitodrineHCID 86603528methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate

Product 1

HCID 11618606{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acidYield 90.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

In a similar manner as described in step 2 of Example 6, the title compound was prepared from methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate (0.17 g, 0.39 mmol), prepar in the previous step, and 1N NaOH (0.59 mL, 0.59 mmol) in 5:5:1 THF:MeOH:water (55 mL) with the exception that this reaction required heating to 65° C. and was complete after 6 hours. The still warm reaction mixture was filtered and then allowed to cool to ambient temperature. The mixture was acidified with 1N HCl (2.5 mL) and the volatiles were removed under reduced pressure (without the addition of heat). The resulting slurry was diluted with water (25 mL) and the solids were isolated by filtration to give {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid as an off-white solid (0.148 g, 90%), mp 258–260° C. (dec). Elemental Analysis for C28H21NO3.0.23 H2O Calc'd: C, 79.39; H, 5.11; N, 3.31. Found: C, 78.84; H 5.03; N, 3.00.

Workup

  1. customThe still warm reaction mixture
  2. filtrationwas filtered
  3. temperatureto cool to ambient temperature
  4. customthe volatiles were removed under reduced pressure (
  5. additionwithout the addition
  6. temperatureof heat)
  7. additionThe resulting slurry was diluted with water (25 mL)
  8. customthe solids were isolated by filtration

Sources & evidence

ORD record
ord-d5a9add9b5fe4aaeba2b838b3950ea22
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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