Sodium Iodide → HCID 22033135, compound

HRID 1792298Notes

Reaction equation

HRID 1792298 reaction equation
[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

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 22033316HCID 22033316, compound

Product 1

HCID 22033135HCID 22033135, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-cefa7890e58d49e19ddeeadc3974c41b
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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