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

HRID 1891437ノート

反応式

HRID 1891437 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-137d1ee2da3445149b9ad20f647f0a5e
出典データセット
uspto-grants-2013_08
特許番号
US08507549B2

反応ノート

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