Potassium Hydroxide → 2-{[6-(3-Pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid

HRID 1359203Notes

Reaction equation

HRID 1359203 reaction equation
[C:1]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]=1[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([O:26][CH:27]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]([O:30]CC)=[O:29])[CH:20]=[CH:19]2)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+]>C1COCC1.O>[C:1]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]=1[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([O:26][CH:27]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]([OH:30])=[O:29])[CH:20]=[CH:19]2)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12082833Ethyl 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate

Product 1

HCID 102067802-{[6-(3-Pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acidYield 73.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate (4.10 g, 7.88 mmol), potassium hydroxide (1.35 g, 24.1 mmol) in THF (66 mL) and water (66 mL) was stirred for 2 hours at room temperature. The mixture was poured into excess water and washed with diethyl ether. The aqueous phase was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was treated with hexane and the formed solid was crystallized from acetonitrile. Drying at 82° C. for 16 hours afforded the title compound as a light yellow solid (2.87 g), mp 144-145° C. Mass spectrum (+ESI, [M+H]+) m/z 493. 1HNMR (500 MHz, DMSO-d6): δ13.1-13.5 (br s, 1H), 8.35 (s, 1H), 7.95-8.05 (m, 2H), 7.9 (d, 1H, J=8.6 Hz), 7.8 (dd, 1H, J=8.6 Hz and 1.7 Hz), 7.7 (dd, 1H, J=7.4 Hz and 0.84 Hz), 7.2-7.45 (m, 9H), 5.2 (q, 2H, J=4.2 Hz), 3.2-3.25 (m, 1H), 2.7 (t, 2H, J=7.3 Hz), 1.5-1.55 (m, 2H), 1.1-1.15 (m, 2H), and 0.7 and ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C32H28O5: Calculated: C, 78.03; H, 5.73; N, 0.00. Found: C, 77.83; H, 5.55; N, 0.02.

Workup

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionThe residue was treated with hexane
  9. customthe formed solid was crystallized from acetonitrile
  10. customDrying at 82° C. for 16 hours

Sources & evidence

ORD record
ord-563da9cd92c641cfb5f7bdb66a57a4bb
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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