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

HRID 1359198Notes

Reaction equation

HRID 1359198 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][CH2:27][C:28]([O:30]CC)=[O:29])[CH:20]=[CH:19]2)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+]>C(O)C.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][CH2:27][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 14798Sodium HydroxideHCID 12082831Ethyl 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate

Product 1

HCID 102945152-{[6-(3-Pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetic acidYield 49.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate (0.743 g, 1.73 mmol) and 1N sodium hydroxide (2.7 mL, 2.7 mmol) in ethanol (15 mL) was stirred at room temperature for 1 hour, 10 minutes. The mixture was diluted with 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 water and brine. It was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue crystallized from methanol and dried for 16 hours at 52° C. to afford 2-{[6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetic acid (0.343 g, 49%), mp 130-132° C. Mass spectrum (−APCl, [M−H]−) m/z 401; 1HNMR (400 MHz, DMSO-d6): δ13.0-13.1 (br s, 1H), 8.35 (d, 1H, J=1.5 Hz), 8.0-8.05 (m, 2H), 7.95 (d, 1H, J=8.8 Hz), 7.8 (dd, 1H, J=8.4 Hz and 1.9 Hz), 7.7 (m, 2H), 7.35-7.45 (m, 3H), 7.3 (dd, 1H, J=8.9 Hz and 2.5 Hz), 4.85 (s, 2H), 2.7 (t, 2H, J=7.4 Hz), 1.5-1.55 (m, 2H), 1.1-1.15 (m, 2H), and 0.7 ppm (t, 3H, J=7.4 Hz). Elemental Analysis for C25H22O5: Calculated: C, 74.61;H, 5.51; N, 0.00. Found: C, 74.29;H, 5.51; N, 0.05.

Workup

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialIt was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue crystallized from methanol
  9. customdried for 16 hours at 52° C.

Sources & evidence

ORD record
ord-af1e830c0ee1432b80e98a0f4f42b8ed
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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