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

HRID 81858

반응식

HRID 81858 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 160960Diamminetetrachlorotitanate(IV)촉매HCID 887Methanol용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5a82a91476764497953c4f8ea7b2279d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846705B2

연결된 노트

불러오는 중…