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

HRID 426171

반응식

HRID 426171 반응식
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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5017029fa6f4407a94fe37d947e3f597
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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