Triethylamine → Bis(4-tert-butylphenyl)iodonium 2-(adamantane-1-carbonyloxy)ethanesulfonate

HRID 1943571

반응식

HRID 1943571 반응식
[S:1]([CH2:5][CH2:6][OH:7])([O-:4])(=[O:3])=[O:2].[Na+].C(N(CC)CC)C.[C:16]12([C:26](Cl)=[O:27])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.S([O-])(O)(=O)=O.[C:34]([C:38]1[CH:43]=[CH:42][C:41]([I+:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:47][CH:46]=2)=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35]>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C)C1C=CN=CC=1.ClCCl.C(C(C)=O)C(C)C>[C:16]12([C:26]([O:7][CH2:6][CH2:5][S:1]([O-:4])(=[O:3])=[O:2])=[O:27])[CH2:23][CH:22]3[CH2:21][CH:20]([CH2:19][CH:18]([CH2:24]3)[CH2:17]1)[CH2:25]2.[C:51]([C:48]1[CH:49]=[CH:50][C:45]([I+:44][C:41]2[CH:40]=[CH:39][C:38]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:43][CH:42]=2)=[CH:46][CH:47]=1)([CH3:54])([CH3:53])[CH3:52]

참가 물질

10

반응물 4

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 517063Sodium IsethionateHCID 20205689Bis(4-tert-butylphenyl)iodanium hydrogen sulfate

생성물 1

HCID 86642239Bis(4-tert-butylphenyl)iodonium 2-(adamantane-1-carbonyloxy)ethanesulfonate수율 95%

시약·촉매·용매 5

HCID 5963Benzyltrimethylammonium chloride촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 7909Methyl Isobutyl Ketone용매

실험 절차

In water, 5.1 g (0.035 mole) of sodium isethionate and 6.4 g (0.053 mole) of benzyltrimethylammonium chloride were mixed and dissolved. The solution was concentrated by removing water in vacuum. The concentrate was dispersed in 55 g of acetonitrile. To the dispersion, 5.2 g (0.052 mole) of triethylamine and 0.42 g (0.0035 mole) of 4-(dimethylamino)pyridine were added, and under ice cooling, 20.6 g (0.052 mole) of 50% adamantane-1-carbonyl chloride in dichloromethane was then added dropwise. The reaction mixture was stirred at room temperature over night. Water was added to quench the reaction, from which acetonitrile was distilled off in vacuum. An amount (0.0088 mole) of bis(4-tert-butylphenyl)iodonium hydrogensulfate prepared in Synthesis Example 1-6 and 50 g of methyl isobutyl ketone were added to the residue, followed by stirring at room temperature for 1 hour. The organic layer was taken out, washed with water, and concentrated in vacuum. Diisopropyl ether was added to the concentrate for recrystallization. The crystals were collected and dried, obtaining the target compound, bis(4-tert-butylphenyl)iodonium 2-(adamantane-1-carbonyloxy)ethanesulfonate. White crystals, 5.7 g, yield 95%. The compound, designated PAG-6, has the following structure.

후처리

  1. dissolutiondissolved
  2. concentrationThe solution was concentrated
  3. customby removing water in vacuum
  4. additionThe concentrate was dispersed in 55 g of acetonitrile
  5. customto quench
  6. customthe reaction
  7. distillationfrom which acetonitrile was distilled off in vacuum
  8. additionwere added to the residue
  9. stirringby stirring at room temperature for 1 hour
  10. washwashed with water
  11. concentrationconcentrated in vacuum
  12. additionDiisopropyl ether was added to the
  13. concentrationconcentrate for recrystallization
  14. customThe crystals were collected
  15. customdried

출처 및 근거

ORD 기록
ord-f071d8395b884546968fc8bf3741de5f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394570B2

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