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

HRID 1359205Notes

Reaction equation

HRID 1359205 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH2:28][C:29]([O:31]CC)=[O:30].[OH-].[Na+]>C(O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH2:28][C:29]([OH:31])=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18182818Ethyl 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate

Product 1

HCID 101407022-{[1-Bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetic acidYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from ethyl 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetate (0.988 g, 1.94 mmol), and sodium hydroxide (3.9 mL, 3.9 mmol) in ethanol (15 mL) in substantially the same manner as described in Step 2 of Example 2. Purification by flash chromatography on acid treated (phosphoric acid) silica gel using 10-40% ethyl acetate in hexane as an eluant and subsequent crystallization from acetonitrile furnished the title compound as a light yellow solid (0.504 g), mp 146-147° C. Mass spectrum (+APCl, [M+H]+) m/z 481. 1HNMR (400 MHz, DMSO-d6): δ13.15-13.3 (br s, 1H), 8.45 (d, 1H, J=1.5 Hz), 8.25 (d, 1H, J=9.0 Hz), 8.15 (d, 1H, J=9.5 Hz), 8.0-8.05 (m, 2H), 7.70-7.75 (m, 1H), 7.4-7.5 (m, 3H), 5.05 (s, 2H), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C25H21BrO5.0.30 H2O: Calculated: C, 61.69;H, 4.47; N, 0.00. Found: C, 61.63;H, 4.12; N, 0.07.

Workup

  1. customPurification by flash chromatography on acid
  2. additiontreated (phosphoric acid) silica gel using 10-40% ethyl acetate in hexane as an eluant
  3. customsubsequent crystallization from acetonitrile

Sources & evidence

ORD record
ord-fc24bea840a949dda7f724082ae252d5
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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