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

HRID 41684

反応式

HRID 41684 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 656671Sodium Pyrosulfite溶媒

反応条件

温度
40 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-6e2393f7454c4ffd9ef3a41c6f75f0c0
出典データセット
uspto-grants-2013_09
特許番号
US08530667B2

関連ノート

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