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

HRID 1359221Notes

Reaction equation

HRID 1359221 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][CH:28]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]([O:31]CC)=[O:30].[OH-].[K+]>C1COCC1.O>[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][CH:28]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]([OH:31])=[O:30]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12082838Ethyl 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate

Product 1

HCID 103034462-{[1-Bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in Step 4 of Example 6, ethyl 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate (1.85 g, 3.09 mmol) was hydrolyzed with potassium hydroxide (0.523 g, 9.32 mmol) in THF (20 mL) and water (20 mL). Crystallization from methylene chloride/hexane and drying at 78° C for 12 hours yielded 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid a bright yellow solid (1.35 g), mp 115-117° C. Mass spectrum (+ESI, [M+H]+) m/z 573; 1HNMR (500 MHz, DMSO-d6): δ13.2-13.5 (br s, 1H), 8.45 (d, 1H, J=1.5 Hz), 8.2 (d, 1H, J=8.9 Hz), 8.1 (d, 1H, J=9.2 Hz), 8.05 (dd, 1H, J=7.7 Hz and 0.7 Hz), 8.0 (dd, 1H, J=8.9 Hz and 1.7 Hz), 7.75 (d, 1H, J=7.8 Hz), 7.4-7.45 (m, 6H), 7.3 (t, 2H, J=7.6 Hz), 7.25 (t, 1H, J=7.4 Hz), 5.35-5.4 (m, 1H), 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=7.4 Hz). Elemental Analysis for C32H27BrO5.0.10H2O: Calculated: C, 67.05; H, 4.78; N, 0.00. Found: C, 66.69; H, 4.38; N, 0.02.

Workup

  1. customCrystallization from methylene chloride/hexane
  2. customdrying at 78° C for 12 hours

Sources & evidence

ORD record
ord-d6b11a48f7c14a79b4f1d04c9d8ce147
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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