Potassium Hydroxide → HCID 10185030, compound

HRID 1359216Notes

Reaction equation

HRID 1359216 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:27]=[CH:26][CH:25]=[CH:24][C:15]=4[C:16]=3[CH2:17][CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:28][CH2:29][C:30]([O:32]CC)=[O:31].[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:27]=[CH:26][CH:25]=[CH:24][C:15]=4[C:16]=3[CH2:17][CH2:18][CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:28][CH2:29][C:30]([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18182797HCID 18182797, compound

Product 1

HCID 10185030HCID 10185030, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in Step 4 of Example 6, ethyl 2-({1-bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthyl}oxy)acetate (0.180 g, 0.345 mmol) was hydrolyzed with potassium hydroxide (0.077 g, 1.4 mmol) in THF (5 mL) and water (5 mL). Crystallization from acetonitrile and drying for 12 hours at 80° C. yielded 2-({1-bromo-6-[3-(2-cyclopentylethyl)-1-benzofuran-2-yl]-2-naphthyl}oxy)acetic acid as a cream-colored solid (0.0807 g), mp 155-156° C. Mass spectrum (−ESI, [M−H]−) m/z 491; 1HNMR (500 MHz, DMSO-d6): δ13.0-13.5 (br s, 1H), 8.35 (d, 1H, J=1.2 Hz), 8.25 (d, 1H, J=8.9 Hz), 8.10 (d, 1H, J=9.0 Hz), 8.05 (dd, 1H, J=9.0 Hz and 1.7 Hz), 7.7 (d, 1H, J=7.8 Hz), 7.6 (d, 1H, J=7.9 Hz), 7.45 (d, 1H, J=9.2 Hz), 7.35-7.4 (m, 1H), 7.30-7.35 (m, 1H), 5.0 (s, 2H), 3.0 (t, 2H, J=7.9 Hz), 1.8-1.9 (m, 1H), 1.7-1.8 (m, 4H), 1.5-1.6 (m, 2H), 1.4-1.5 (m, 2H), and 1.15-1.25 ppm (m, 2H). Elemental Analysis for C27H25BrO4: Calculated: C, 65.13; H, 5.16; N, 0.00. Found: C, 64.83; H, 4.94; N, 0.06.

Workup

  1. customCrystallization from acetonitrile
  2. customdrying for 12 hours at 80° C.

Sources & evidence

ORD record
ord-9941869753f446bbae78bfde4a7fd86c
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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