Potassium Carbonate → HCID 44603676, compound

HRID 1044444Notes

Reaction equation

HRID 1044444 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[C:19]([O:21][CH2:22][O:23][CH3:24])[CH:18]=[CH:17][C:16]=1[C:25](=[O:28])[CH2:26]I)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CC(C)=O>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:1][OH:4])=[C:19]([CH:20]=1)[O:21][CH2:26][C:25]([C:16]1[CH:17]=[CH:18][C:19]([O:21][CH2:22][O:23][CH3:24])=[CH:20][C:15]=1[O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:28])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 25138420HCID 25138420, compound

Product 1

HCID 44603676HCID 44603676, compoundYield 144.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (0.165 g, 1.2 mmol) was added to a solution of 1-[2-benzyloxy-4-(methoxymethyloxy)phenyl]-2-iodo-ethanone (0.412 g, 1 mmol) and 4-benzyloxy-salicylalchohol (0.254 g, 1.1 mmol) in 10 mL of acetone and the mixture refluxed for 10 hours. After completion of the reaction (TLC), the solvent was evaporated and the residue extracted with EtOAc:water (2×20 mL:20 mL). The organic layers were combined, dried over sodium sulfate and evaporated. The residue was chromatographed over silica using hexanes:EtOAc (2:1). The organic fractions were evaporated to provide 0.371 g (72%) of white solid: mp 115-118° C.; TLC Rf0.16 in hexanes:EtOAc (2:1); 1H NMR (600 MHz, CDCl3) δ 7.88-7.86 (d, 1H, J=9 Hz, Ar—H5), 7.64-7.25 (m. 10H, 2×C6H5), 7.21-7.20 (d, 1H, J=8.4 Hz, Ar—H6′), 6.92 (d, 1H, J=2.4 Hz, Ar—H8), 6.78-6.76 (dd, 1H, 2J=9 Hz, 3J=2.4 Hz, Ar—H6), 6.56-6.54 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5′), 6.26-6.25 (d, 1H, J=2.4 Hz, Ar—H3′), 5.30 (s, 4H, PhCH2), 5.21 (s, 2H, O—CH2—O), 4.98 (s, 2H, H-2), 4.57-4.56 (d, 2H, J=6 Hz, CH2OH), 4.13-4.11 (t, 1H, CH2OH), 3.44 (s, 3H, OCH3); 13C NMR (100 MHz, CDCl3) δ 194.6, 164.4, 162.2, 160.7, 158.6, 138.9, 137.6, 133.6, 130.2, 129.9, 129.8, 129.2, 125.1, 120.4, 110, 106.8, 102.5, 101.7, 95.6, 75.3, 72.4, 71.2, 61.5, 56.9; analysis calcd. for C31H30O7. C, 72.36; H, 5.88. found: C, 72.1; H, 5.85.

Workup

  1. temperaturethe mixture refluxed for 10 hours
  2. customAfter completion of the reaction (TLC)
  3. customthe solvent was evaporated
  4. extractionthe residue extracted with EtOAc
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed over silica
  8. customThe organic fractions were evaporated

Sources & evidence

ORD record
ord-c9548fae43134885baf57abcea171051
Source dataset
uspto-grants-2013_10
Patent number
US08563599B2

Reaction notes

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