p-Toluenesulfonic acid monohydrate → 2-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole

HRID 7731

反応式

HRID 7731 の反応式
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([O:17][CH3:18])[CH:11]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:18][O:17][C:12]1[CH:11]=[C:10]([C:9]2[O:19][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N:8]=2)[CH:15]=[CH:14][C:13]=1[CH3:16]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 16378794N-(2-Hydroxyphenyl)-3-methoxy-4-methylbenzamide

生成物 1

HCID 219909682-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of N-(2-hydroxyphenyl)-3-methoxy-4-methylbenzamide (1.5 g, 5.8 mmol), toluene (30 mL), p-toluenesulfonic acid monohydrate (7.6 g, 40 mmol) and molecular sieves was refluxed overnight. After cooling reaction to rt, filtered washing with warm chloroform and concentrated filtrate in vacuo. The resulting brown oil was purified by flash chromatography on silica gel using 1:4 EtOAc:hexanes to give the desired intermediate, 2-(3-methoxy-4-methylphenyl)-1,3-benzoxazole, as a colorless solid.

後処理

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customreaction to rt
  4. filtrationfiltered
  5. washwashing with warm chloroform and concentrated filtrate in vacuo
  6. customThe resulting brown oil was purified by flash chromatography on silica gel using 1:4 EtOAc

出典と根拠

ORDレコード
ord-04560bce4f774e089189eeafb357a37c
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

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