Sulfuric Acid → 7-Isopropyl-2,4-dimethyl-benzooxazol-6-ol

HRID 38443

反応式

HRID 38443 の反応式
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([CH:10]([CH3:12])[CH3:11])[C:3]=1[OH:13].O[C:15]1C=C(C(C)C)C=C(O)[C:20]=1C.C1(C)CC(=O)C(C(C)C)C(=O)C1.C(OC(OCC)OCC)C.OS(O)(=O)=O>CO.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[CH:10]([C:4]1[C:3]2[O:13][C:15]([CH3:20])=[N:1][C:2]=2[C:7]([CH3:8])=[CH:6][C:5]=1[OH:9])([CH3:11])[CH3:12]

参加物

8

反応物 5

HCID 1118Sulfuric AcidHCID 31214Ethyl orthoformateHCID 119881382-Isopropyl-5-methylcyclohexane-1,3-dioneHCID 23345336CymorcinHCID 595987544-Amino-2-isopropyl-5-methyl-benzene-1,3-diol

生成物 1

HCID 595986327-Isopropyl-2,4-dimethyl-benzooxazol-6-ol

試薬・触媒・溶媒 2

HCID 160960Diamminetetrachlorotitanate(IV)触媒HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

To a flask charged with 4-amino-2-isopropyl-5-methyl-benzene-1,3-diol (250 mg, 1.4 mmol) (Treibs and Albrecht, “The dihydroxycymenes. IV. Isocymorcin (3,5-dihydroxycymene) from 3,5-menthanedione by dehydrogenation and total synthesis,” Journal fuer Praktische Chemie (1961), 13, 291-305), purged with argon, and cooled to 0° C., was sequentially added triethylorthoformate (0.53 mL, 4.2 mmol), MeOH (2.5 mL), and a 10% v/v solution of H2SO4 in MeOH (25 μL). The reaction was allowed to warm to room temperature slowly, stirred overnight, quenched with saturated NaHCO3, and concentrated. The residue was partitioned between water and methylene chloride. The combined organic phases were dried with Na2SO4 and concentrated. Purification via flash chromatography afforded 175 mg of 7-isopropyl-2,4-dimethyl-benzooxazol-6-ol.

後処理

  1. custompurged with argon
  2. temperatureto warm to room temperature slowly
  3. customquenched with saturated NaHCO3
  4. concentrationconcentrated
  5. customThe residue was partitioned between water and methylene chloride
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. concentrationconcentrated
  8. customPurification via flash chromatography

出典と根拠

ORDレコード
ord-f48841bbb421402992e308f5406e6763
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

関連ノート

読み込み中…