Sodium Iodide → HCID 22033135, 화합물

HRID 1792298노트

반응식

HRID 1792298 반응식
[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

참가 물질

5

반응물 2

HCID 5238Sodium IodideHCID 22033316HCID 22033316, 화합물

생성물 1

HCID 22033135HCID 22033135, 화합물수율 92%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6569Methyl Ethyl Ketone용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-cefa7890e58d49e19ddeeadc3974c41b
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

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