Iodine → 4-Iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

HRID 41684

반응식

HRID 41684 반응식
[CH3:1][O:2][C:3]1[CH:11]2[CH:6]([CH:7]3[O:12][CH:10]2[CH2:9][CH2:8]3)[C:5](=[O:13])[CH:4]=1.[N+]([O-])([O-])=O.[NH4+].[Ce].[I:20]I>S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[I:20][C:4]1[C:5](=[O:13])[CH:6]2[CH:11]([C:3]=1[O:2][CH3:1])[CH:10]1[O:12][CH:7]2[CH2:8][CH2:9]1

참가 물질

5

반응물 3

HCID 807IodineHCID 57418452Ammonium cerium-nitrateHCID 672834435-Methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

생성물 1

HCID 685690024-Iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one수율 84.6%

시약·촉매·용매 1

HCID 656671Sodium Pyrosulfite용매

반응 조건

온도
40 °C

실험 절차

A flask is charged with 5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (3.96 g, 22 mmol), cerium ammonium nitrate (13.3 g, 24.2 mmol) and iodine (6.73 mg, 26.5 mmol) and then purged with nitrogen. Anhydrous acetonitrile (120 ml) is added, and the reaction heated to 40° C., with stirring for 2 hours. The crude reaction mixture is poured onto a saturated aqueous solution of sodium metabisulphite (250 ml) and extracted with dichloromethane (2×250 ml). The combined organics are dried over magnesium sulphate, filtered, and the solvent is removed under reduced pressure to give 4-Iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (5.70 g)

후처리

  1. custompurged with nitrogen
  2. additionAnhydrous acetonitrile (120 ml) is added
  3. customThe crude reaction mixture
  4. extractionextracted with dichloromethane (2×250 ml)
  5. dry with materialThe combined organics are dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure

출처 및 근거

ORD 기록
ord-6e2393f7454c4ffd9ef3a41c6f75f0c0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530667B2

연결된 노트

불러오는 중…