(3-Hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanone → 3-[5-Isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-benzaldehyde

HRID 426193ノート

反応式

HRID 426193 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:16]([CH:17]([CH3:19])[CH3:18])=[C:15]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:14]=[C:13]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH:17]([C:16]1[C:11]([C:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH:2]=[O:1])=[O:10])=[N:12][C:13]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[N:14][C:15]=1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)([CH3:19])[CH3:18]

参加物

3

反応物 2

HCID 59184693(3-Hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanoneHCID 178418287HCID 178418287、化合物

生成物 1

HCID 591848203-[5-Isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-benzaldehyde収率 94.4%

実験手順

A mixture of (3-hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanone (1.9 g, 3.52 mmol), pyridinium chlorochromate (1.14 g, 5.28 mmol), and dried celite (1 g) in dichloromethane (20 ml) was stirred for 1 hr. at room temperature. The mixture was then filtered through a short silica gel pad and the pad was washed with EA. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4)) to afford 1.75 g (74%) of a pale yellow syrup. 1H NMR (200 MHz, CDCl3) δ 1.19 (6H, d, J=7.4 Hz), 2.88 (1H, m), 3.79 (3H, s), 3.83 (3H, s), 5.29 (2H, s), 5.45 (2H, s), 6.77-6.95 (4H, m), 7.28-7.42 (4H, m), 7.65 (1H, m), 8.11-8.28 (3H, m), 10.03 (1H, s).

後処理

  1. dry with materialdried celite (1 g) in dichloromethane (20 ml)
  2. customat room temperature
  3. filtrationThe mixture was then filtered through a short silica gel pad
  4. washthe pad was washed with EA
  5. customThe combined filtrate was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4))

出典と根拠

ORDレコード
ord-2850a8a07a604cad86c7281b89affbde
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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