Iodine → HCID 86667579、化合物

HRID 85286ノート

反応式

HRID 85286 の反応式
[CH2:1]([N:5]([CH2:23][CH2:24][CH2:25][CH3:26])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][CH:14]=[CH:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[C:8]([O:21][CH3:22])[CH:7]=1)[CH2:2][CH2:3][CH3:4].C([Li])CCC.CN(C)[CH:34]=[O:35].II>O1CCCC1.CCOCC.C(OCC)(=O)C.O>[CH2:23]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][CH:14]=[CH:15][C:16]2[S:17][C:18]([CH:34]=[O:35])=[CH:19][CH:20]=2)=[C:8]([O:21][CH3:22])[CH:7]=1)[CH2:24][CH2:25][CH3:26]

参加物

9

反応物 4

HCID 807IodineHCID 6228DimethylformamideHCID 86667578HCID 86667578、化合物HCID 178418339Butyllithium

生成物 1

HCID 86667579HCID 86667579、化合物収率 80.1%

試薬・触媒・溶媒 4

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-69 °C

実験手順

In a stream of argon, in 13 ml of tetrahydrofuran was dissolved 0.83 g (2.25 mmol) of dibutyl[3-methoxy-4-[4-(thiophene-2-yl)-1,3-butadienyl]phenyl]amine, and 2.1 ml of n-butyllithium (1.6 mol solution in hexane) (3.36 mmol) was added dropwise thereto under cooling at −68 to −70° C. After the mixture was stirred for 30 minutes, 0.21 ml (2.87 mmol) of N,N-dimethylformamide was added dropwise thereto. The reaction mixture was stirred for 1.5 hours and the temperature was allowed to rise. To this mixture, 5 ml of water was added dropwise. After the reaction mixture was poured into 50 ml of water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residual liquid was purified by silica gel column chromatography to give a dark reddish brown oily matter. After this oily matter was dissolved in 100 ml of ether, 600 mg of iodine was added thereto and the mixture was stirred. The mixture was washed with a 5% sodium bisulfite solution and then with a saturated saline solution. Drying over anhydrous sodium sulfate and concentration were performed. The residue was purified by silica gel column chromatography to give 715 mg of a dark reddish brown liquid (yield: 80.1%).

後処理

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred for 1.5 hours
  3. washwashing with a saturated saline solution
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration
  5. customThe residual liquid was purified by silica gel column chromatography
  6. customto give a dark reddish brown oily matter
  7. stirringthe mixture was stirred
  8. washThe mixture was washed with a 5% sodium bisulfite solution
  9. dry with materialDrying over anhydrous sodium sulfate and concentration
  10. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-63979f3a24fa453283f06c7afe9e803f
出典データセット
uspto-grants-2014_09
特許番号
US08846955B2

反応ノート

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