Sodium Iodide → HCID 22033135、化合物

HRID 1792298ノート

反応式

HRID 1792298 の反応式
[OH:1][C:2]1([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37]Cl)=[CH:28][CH:27]=2)[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][O:14][CH3:15])=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:18][CH:17]=1.[I-:39].[Na+]>CC(=O)CC.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[I:39][CH2:37][CH2:36][O:35][CH2:34][CH2:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([C:2]2([OH:1])[C:11]3[C:6](=[CH:7][C:8]([O:12][CH2:13][O:14][CH3:15])=[CH:9][CH:10]=3)[O:5][CH2:4][CH:3]2[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:21]=2)=[CH:31][CH:30]=1

参加物

5

反応物 2

HCID 5238Sodium IodideHCID 22033316HCID 22033316、化合物

生成物 1

HCID 22033135HCID 22033135、化合物収率 92%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

4-Hydroxy-4-{4-[2-(2-chloroethoxy)ethoxy]phenyl}-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]chroman (490 mg, 0.9 mmol) was dissolved in 2-butanone (30 ml) under argon atmosphere. Then, sodium iodide (1.4 g, 9.3 mmol) and tetrabutylammonium iodide (1.6 g, 4.5 mmol) were added thereto, and the mixture was refluxed for 16 hours. The reaction solution was cooled down to normal temperature, concentrated, and diluted with ethyl acetate. Then, in order to eliminate the resulting NaCl and the excess sodium iodide and tetrabutylammonium iodide, the solution was filtered. The filtrate was concentrated under reduced pressure, and the residue was subjected to flash column chromatography (n-hexane:ethyl acetate=4:1→2:1) to give the title compound (527 mg, yield 90%) which is pale yellow and sticky. Mass [M−H2O]+=619 Step 3) Synthesis of 4-hydroxy-4-{4-{2-[2-(4,4,5,5,5-pentafluoropentylthio)ethoxy]ethoxy}phenyl}-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]chroman

後処理

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperatureThe reaction solution was cooled down to normal temperature
  3. concentrationconcentrated
  4. additiondiluted with ethyl acetate
  5. filtrationthe excess sodium iodide and tetrabutylammonium iodide, the solution was filtered
  6. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-cefa7890e58d49e19ddeeadc3974c41b
出典データセット
uspto-grants-2006_07
特許番号
US07074819B2

反応ノート

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