tert-Butanol → tert-Butyl-2-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)acetate

HRID 2403072

Reaktionsgleichung

Reaktionsgleichung von HRID 2403072
[CH:1]1[C:2]([CH2:19][C:20]([OH:22])=[O:21])=[CH:3][C:4]([I:18])=[C:5]([O:8][C:9]2[CH:10]=[C:11]([I:17])[C:12]([OH:16])=[C:13]([I:15])[CH:14]=2)[C:6]=1[I:7].[C:23](O)([CH3:26])([CH3:25])[CH3:24].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1.CN(C)C1C=CN=CC=1>[C:23]([O:21][C:20](=[O:22])[CH2:19][C:2]1[CH:1]=[C:6]([I:7])[C:5]([O:8][C:9]2[CH:10]=[C:11]([I:17])[C:12]([OH:16])=[C:13]([I:15])[CH:14]=2)=[C:4]([I:18])[CH:3]=1)([CH3:26])([CH3:25])[CH3:24]

Komponenten

6

Edukt 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 65552Tetraiodothyroacetic acid

Produkt 1

HCID 44224192tert-Butyl-2-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)acetateAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In anhydrous conditions, Tetrac (30.0 g, 40.1 mmol, 1.0 eq.) was dissolved in anhydrous dioxane (200 mL). Tert-butyl alcohol (11.4 mL, 120.3 mmol, 3.0 eq.) and 4-dimethylaminopyridine (3.9 g, 32.1 mmol, 0.8 eq.) were then added. The solution was stirred and dicyclohexylcarbodiimide (9.1 g, 44.1 mmol, 1.1 eq.) was added over a 5 minutes period. The mixture was stirred for 3 hours at room temperature. The cyclohexylurea that has precipitated was removed by filtration through a fritted Büchner funnel, and the filtrate was washed with 10% potassium bicarbonate solution (2×100 mL). During this procedure, some additional cyclohexylurea precipitated and was removed by filtration of both layers to facilitate their separation. The organic solution was then dried over magnesium sulfate, filtered and then evaporated with a rotary evaporator to obtain the crude product as a yellow powder which was purified by column chromatography (DCM/cyclohexane 90/10) to yield tert-butyl-2-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)acetate (3.2 g, 4.0 mmol) as a solid.

Aufarbeitung

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. customThe cyclohexylurea that has precipitated
  3. customwas removed by filtration through a fritted Büchner funnel
  4. washthe filtrate was washed with 10% potassium bicarbonate solution (2×100 mL)
  5. customDuring this procedure, some additional cyclohexylurea precipitated
  6. customwas removed by filtration of both layers
  7. customtheir separation
  8. dry with materialThe organic solution was then dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated with a rotary evaporator
  11. customto obtain the crude product as a yellow powder which
  12. customwas purified by column chromatography (DCM/cyclohexane 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-063a440dee1d4bde91da9574c7d8ef6e
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802240B2

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