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

HRID 2403072

反应方程式

HRID 2403072 反应方程式
[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]

参与物

6

反应物 3

HCID 6386叔丁醇HCID 10868N,N'-二环己基碳二亚胺HCID 65552四碘甲状腺乙酸

产物 1

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

试剂、催化剂与溶剂 2

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 312751,4-二氧六环溶剂

实验过程

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.

后处理

  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)

来源与证据

ORD记录
ord-063a440dee1d4bde91da9574c7d8ef6e
来源数据集
uspto-grants-2014_08
专利号
US08802240B2

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