Potassium Hydroxide → HCID 10159240, compound

HRID 1359236Notes

Reaction equation

HRID 1359236 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]3[O:17][C:18]4[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=4[C:20]=3[C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:12]=2)[CH:7]=1.[OH-].[K+]>C1COCC1.CO>[C:21]([C:20]1[C:19]2[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=2[O:17][C:16]=1[C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])[CH:15]=[CH:14]2)(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12082841HCID 12082841, compound

Product 1

HCID 10159240HCID 10159240, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of {[6-(3-benzoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetic acid methyl ester (0.128 g, 0.293 mmol) in THF:MeOH (3:2, 10 mL) at 0° C. was added 1 N KOH (0.879 mL, 0.879 mmol) dropwise. The reaction was stirred at this temperature for 0.25 h and then warmed to room temperature for 1 h. After concentration, the residue was diluted with H2O, and this mixture was acidified to pH 1 with 2 N HCl. After stirring at room temperature for 3 h, the solid was filtered and washed with excess H2O and hexane. At this point, the compound was dried under high vacuum to afford the product (0.116 g) as a yellow solid, mp 178-181° C. Mass spectrum (−APCl, [M−H]−) m/z 421. 1HNMR (500 MHz, DMSO-d6): δ11.05-14.15 (br s, 1H), 8.17 (d, J=1.5 Hz, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.76-7.81 (m, 3H), 7.70 (d, J=8.8 Hz, 1H), 7.52-7.57 (m, 2H), 7.42-7.51 (m, 2H), 7.31-7.37 (m, 3H), 7.18-7.24 (m, 2H), and 4.77 ppm (s, 2H). Elemental Analysis for C27H18O5.0.5H2O: Calculated: C, 75.17; H, 4.44; N, 0.00 Found: C, 75.03; H, 4.34; N, 0.14

Workup

  1. concentrationAfter concentration
  2. additionthe residue was diluted with H2O
  3. stirringAfter stirring at room temperature for 3 h
  4. filtrationthe solid was filtered
  5. washwashed with excess H2O and hexane
  6. customAt this point, the compound was dried under high vacuum

Sources & evidence

ORD record
ord-fedfef820db4429d9fc76c9e6f4d006d
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

Loading…