Iodine → 7,8-Difluoro-5-iodo-6-methoxymethoxy-2-pentylchroman

HRID 2244840ノート

反応式

HRID 2244840 の反応式
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[CH:4][C:3]=1[O:18][CH2:19][O:20][CH3:21].[Li]CCCC.[I:27]I.S([O-])(O)=O.[Na+]>C1COCC1.CC(OC)(C)C>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4]([I:27])[C:3]=1[O:18][CH2:19][O:20][CH3:21]

参加物

7

反応物 4

HCID 807IodineHCID 23665763Sodium BisulfiteHCID 592152597,8-Difluoro-6-methoxymethoxy-2-pentylchromanHCID 178418339Butyllithium

生成物 1

HCID 592152607,8-Difluoro-5-iodo-6-methoxymethoxy-2-pentylchroman

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 15413tert-Butyl methyl ether溶媒

実験手順

17.7 g (58.9 mmol) of 7,8-difluoro-6-methoxymethoxy-2-pentylchroman are initially introduced in 370 ml of THF, and 47.7 ml (75.9 mmol) of n-BuLi (15% soln. in hexane) are added dropwise at −78° C. When the addition is complete, the mixture is stirred at this temperature for 30 min and subsequently at room temperature for 1 h. The solution is re-cooled to −78° C., and a solution of 17.9 g (70.7 mol) of iodine in 100 ml of THF is added dropwise. The reaction mixture is stirred at room temperature for 90 min and subsequently diluted with MTBE. Sat. sodium hydrogensulfite soln. is added to the mixture, which is subsequently washed with water and sat. sodium chloride soln. The crude product remaining after drying using sodium sulfate and removal of the solvents is purified by column chromatography (SiO2, n-heptane:MTBE=3:1), giving 7,8-difluoro-5-iodo-6-methoxymethoxy-2-pentylchroman as a brown oil.

後処理

  1. additionWhen the addition
  2. temperatureThe solution is re-cooled to −78° C.
  3. stirringThe reaction mixture is stirred at room temperature for 90 min
  4. additionis added to the mixture, which
  5. washis subsequently washed with water and sat. sodium chloride soln
  6. customafter drying
  7. customsodium sulfate and removal of the solvents
  8. customis purified by column chromatography (SiO2, n-heptane:MTBE=3:1)

出典と根拠

ORDレコード
ord-ac281643d9814b7fac09eece3ac33200
出典データセット
uspto-grants-2010_03
特許番号
US07678929B2

反応ノート

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