Sodium Iodide → HCID 20790071, compound

HRID 2183432Notes

Reaction equation

HRID 2183432 reaction equation
[C:1]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:16][C:17]([O-])([CH3:19])[CH3:18].[K+].[I-].[Na+]>C(O)(C)(C)C>[CH2:16]([O:4][CH2:3][CH2:2][CH:2]([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[C:1]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:17]1[CH:19]=[CH:8][CH:6]=[CH:7][CH:18]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 68324Di-tert-butyl malonateHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 20790071HCID 20790071, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

Di(tert-butyl) malonate (151.4 g, 686 mmol) was added dropwise at 50° C. to a suspension of potassium tert-butylate (77 g, 686 mmol) in 500 ml of tert-butanol. Sodium iodide (10.33 g) was then added, followed by dropwise addition of Intermediate 5C (117.1 g, 686 mmol) at 40-50° C. The resulting thick suspension was stirred at 70° C. for two days. During this time, two further portions of potassium tert-butylate (15.4 g each, 70 mmol) were added. The mixture was then poured into ice-water and extracted three times with diethyl ether. The organic layers were dried over Na2SO4, filtered and evaporated. The crude product was finally purified by column chromatography using a cyclohexane/ethyl acetate gradient (70:1→15:1).

Workup

  1. extractionextracted three times with diethyl ether
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was finally purified by column chromatography

Sources & evidence

ORD record
ord-d29088710fb9485b9a40befbb63e3732
Source dataset
uspto-grants-2005_05
Patent number
US06900194B1

Reaction notes

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