Potassium Carbonate → 2-{5-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenoxy}-1-(4-benzyloxy-phenyl)-ethanone

HRID 1891437Notes

Reaction equation

HRID 1891437 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH2:22]I)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([CH:40]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[CH:44][CH:43]=2)[OH:41])=[C:37]([OH:39])[CH:38]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([CH:40]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[CH:44][CH:43]=2)[OH:41])=[C:37]([CH:38]=1)[O:39][CH2:22][C:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:16][CH:17]=1)=[O:24])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 674984815-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenolHCID 866649211-(4-Benzyloxy-phenyl)-2-iodo-ethanone

Product 1

HCID 674988732-{5-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenoxy}-1-(4-benzyloxy-phenyl)-ethanoneYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (0.165 g, 1.2 mmol) was added to a solution of 1-(4-benzyloxy-phenyl)-2-iodo-ethanone (P4) (0.352 g, 1 mmol) and 5-benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenol (P3) (0.412 g, 1 mmol) were in 40 mL of dry acetone and the mixture was refluxed for 6 hr. After completion of reaction (TLC), the solvent was evaporated and the residue extracted with EtOAc:water (3×40 mL). The organic layers were combined, dried over sodium sulfate and evaporated. The residue was dissolved in EtOAc and chromatographed over silica using hexanes: EtOAc (4:1) to give (0.381 g, 60%) yellowish solid product T3. 1H NMR (400 MHz, CDCl3) δ, 7.88 (d, 2H , J=8.8 Hz, Ar—H2/6), 7.41-7.29 (m, 17H, 2×Ar—H, 3×C6H5), 7.07(d, 1H, J=8.8 Hz, 8.4 Hz), 7.02(d, 2H, J=8.8 Hz, Ar—H3/5), 6.92(d, 2H, J=8.8 Hz, 2×Ar—H), 6.54(dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H4′), 6.5 (d, 1H, J=2.4 Hz, Ar—H6′), 6.04 (d, 1H, J=5.6 Hz, CH—OH), 5.24(m, 2H2O—CH2), 5.13 (s, 2H, PhCH2), 5.04 (s, 2H, PhCH2), 5.0 (s, 2H, PhCH2).

Workup

  1. temperaturethe mixture was refluxed for 6 hr
  2. customAfter completion of reaction (TLC)
  3. customthe solvent was evaporated
  4. extractionthe residue extracted with EtOAc
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. dissolutionThe residue was dissolved in EtOAc
  8. customchromatographed over silica

Sources & evidence

ORD record
ord-137d1ee2da3445149b9ad20f647f0a5e
Source dataset
uspto-grants-2013_08
Patent number
US08507549B2

Reaction notes

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