Sodium Iodide → Allyl 4-iodomethyl-methyl-1-cyclohexanecarboxylate

HRID 2225501

반응식

HRID 2225501 반응식
[I-:1].[Na+].S(O[CH2:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:21])([C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH2:11][CH2:10]1)(C)(=O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[I:1][CH2:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:21])([C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH2:11][CH2:10]1

참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 19004719Allyl 4-mesyloxymethyl-1-methyl-1-cyclohexanecarboxylate

생성물 1

HCID 19004693Allyl 4-iodomethyl-methyl-1-cyclohexanecarboxylate수율 49.6%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

5 g of sodium iodide was added to a solution of 2 g of allyl 4-mesyloxymethyl-1-methyl-1-cyclohexanecarboxylate (Example 45) in 50 ml of acetone. The solution was reacted for 4 hours, while it was refluxed. After reaction, 100 ml of an aqueous sodium thiosulfate solution was added to the reaction solution. The solution was extracted three times with 30 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium thiosulfate solution and twice with an aqueous sodium chloride solution, and was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 10 g of silica gel. From the fraction eluted with hexane and ethyl acetate=2:1, the solvent was removed in vacuo, yielding 1.1 g of allyl 4-iodomethyl-1-methyl-1-cyclohexanecarboxylate as a pale yellow oil, which had the following physiochemical properties:

후처리

  1. customThe solution was reacted for 4 hours, while it
  2. temperaturewas refluxed
  3. additionwas added to the reaction solution
  4. extractionThe solution was extracted three times with 30 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed twice with an aqueous sodium thiosulfate solution and twice with an aqueous sodium chloride solution
  7. dry with materialwas dried over magnesium sulfate
  8. customThereafter, the solvent was removed in vacuo
  9. customThe oily substance obtained
  10. washFrom the fraction eluted with hexane and ethyl acetate=2:1
  11. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-f37a82d7fe964bbfa9bde494268ab89c
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05344845

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