Dimethylformamide → Benzoic acid 3,5-dimethyl-benzyl ester

HRID 426171

反応式

HRID 426171 の反応式
ClC1N=C(Cl)C(C(C)C)=C(O[C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)N=1.[C:21]([O-:29])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na+].[CH3:31]N(C=O)C>>[CH3:20][C:15]1[CH:16]=[C:17]([CH:18]=[C:13]([CH3:31])[CH:14]=1)[CH2:19][O:28][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 517055Sodium BenzoateHCID 189252522,4-Dichloro-6-(3,5-dimethyl-phenoxy)-5-isopropyl-pyrimidine

生成物 1

HCID 13146856Benzoic acid 3,5-dimethyl-benzyl ester収率 71%

実験手順

A mixture of 3,5-dimethylbenzyl bromide (2, 39.8, 0.2M) and sodium benzoate (34.56 g, 0.24M) in anhydrous DMF (400 ml) was stirred at room temperature for overnight. The mixture was then partitioned between ether and water. The organic layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a pale yellow oil. The crude product was purified by silica gel column chromatography (eluent, hexane) to afford 32 g (71%) of a colorless oil. 1H NMR (200 MHz, CDCl3) δ 2.33 (6H, s), 5.29 (2H, s), 6.98 (1H, s), 7.05 (2H, s), 7.38-7.59 (3H, m), 8.05-8.11 (2H, m).

後処理

  1. customThe mixture was then partitioned between ether and water
  2. washwashed with water twice
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a pale yellow oil
  7. customThe crude product was purified by silica gel column chromatography (eluent, hexane)

出典と根拠

ORDレコード
ord-5017029fa6f4407a94fe37d947e3f597
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

関連ノート

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