Potassium Carbonate → HCID 86748477, compound

HRID 275184Notes

Reaction equation

HRID 275184 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]([C:12]2[C:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:15]=[CH:14][C:13]=2[OH:24])[CH:9]=[CH:10][CH:11]=1)([O:3][CH2:4][CH3:5])=[O:2].[C:25]12([C:35]3[CH:42]=[CH:41][C:38]([CH2:39]I)=[CH:37][C:36]=3[O:43][CH3:44])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[C:1]([C:6]1[CH:7]=[C:8]([C:12]2[C:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:15]=[CH:14][C:13]=2[O:24][CH2:39][C:38]2[CH:41]=[CH:42][C:35]([C:25]34[CH2:34][CH:29]5[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]5)[CH2:26]3)[CH2:32]4)=[C:36]([O:43][CH3:44])[CH:37]=2)[CH:9]=[CH:10][CH:11]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20090642HCID 20090642, compoundHCID 86748478HCID 86748478, compound

Product 1

HCID 86748477HCID 86748477, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

Phenol 25 (0.656 g., 2.00 mmol, 1 equiv.; from Example 18) is dissolved in 15 mL of methyl isobutyl ketone. 4-[1-Adamantyl]-3-methoxybenzyl iodide (18b) (0.766 g., 2.00 mmol, 1 equiv.) and potassium carbonate (1.00 g., 7.2 mmol, 3.6 equiv.) are added and the mixture is heated to reflux for 5 hours. The solvents are evaporated and the residue is dissolved in methylene chloride. This solution is washed with water and brine, then dried (MgSO4), and concentrated. The crude material is chromatographed on silica gel using 50% CH2Cl2 /hexane to afford 3'-carboethoxy-2-[4-(1-adamantyl)-3-methoxyphenyl]methoxy-[1,1'-biphenyl]-6-acetic acid, ethyl ester (29d) (0.725 g., 1.24 mmol, 62%): 1H NMR (300 MHz, CDCl3) δ 8.06 (dd, J=2, 8 Hz, 1H, ArH), 7.98 (s, 1H, ArH), 7.50-7.47 (m, 2H, ArH), 7.33-6.97 (m, 4H, ArH), 6.69 (dd, J=2, 8 Hz, 1H, ArH), 6.57 (d, J=2 Hz, 1H, ArH), 4.97 (s, 2H, ArCH2O), 4.38 (q, J=7 Hz, 2H, CO2CH2), 4.03 (q, J=7 Hz, 2H, CO2CH2), 3.59 (s, 3H, CH3O), 3.41 (s, 2H, ArCH2CO2), 2.03 (s, 9H, adamantyl), 1.75 (s, 6H, adamantyl), 1.40 (t, J=7 Hz, 3H, CO2CH2CH3), 1.16 J=7 Hz, 3 Hz, CO2CH2CH3); 13C NMR (75 MHz, CDCl3) δ 171.48 (C=O), 166.54 (C=O), 158.84, 156.13, 137.62, 137.33, 135.74, 134.91, 134.21, 131.31, 131.05, 130.44, 128.82, 128.33, 128.14, 126.27, 122.82, 118.09, 111.49, 109.54, 69.75, 60.97, 60.77, 54.82, 40.55, 39.23, 37.13, 36.80, 29.09, 14.38, 14.12.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 5 hours
  3. customThe solvents are evaporated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. washThis solution is washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude material is chromatographed on silica gel using 50% CH2Cl2 /hexane

Sources & evidence

ORD record
ord-a5d232dfb3ac4a3492505b7212c5149e
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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