홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

p-Toluenesulfonic acid → HCID 54114972, 화합물

HRID 1109365
노트
인쇄 미리보기

반응식

HRID 1109365 반응식
[CH3:1][O:2][N:3]([CH3:14])[C:4]([N:6]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][C:7]1=[O:13])=[O:5].C[Si](C)(C)N[Si](C)(C)C.[Li].[C:25]([C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:36]=1[O:37][Si](C)(C)C)[CH:32]=O)([CH3:28])([CH3:27])[CH3:26].C1(C)C=CC(S(O)(=O)=O)=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C1COCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][N:3]([CH3:14])[C:4]([N:6]1[C:10]([CH3:12])([CH3:11])[CH2:9][C:8](=[CH:32][C:31]2[CH:30]=[C:29]([C:25]([CH3:26])([CH3:28])[CH3:27])[C:36]([OH:37])=[C:35]([C:42]([CH3:45])([CH3:44])[CH3:43])[CH:34]=2)[C:7]1=[O:13])=[O:5]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 6

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 18991206HCID 18991206, 화합물HCID 19022148HCID 19022148, 화합물HCID 57426343Lithium bis(trimethylsilyl)amide

생성물 1

HCID 54114972
HCID 54114972, 화합물
수율 29%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매4회

실험 절차

To a chilled solution (-70° C.) of 453 mg (2.26 mmol) of the thus obtained 1-(N-methoxy-N-methylcarbamoyl)-5,5-dimethylpyrrolidin-2-one in THF (12 ml) was added 2.26 ml (2.26 mmol) of a THF solution of 1.0M lithium hexamethyldisilazane while being stirred under a nitrogen atmosphere. Five minutes later, 693 mg (2.26 mmol) of 3,5-di-tert-butyl-4-trimethylsiloxybenzaldehyde was added thereto and the mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was then poured into ice-water and extracted with dichloromethane. The dichloromethane layer was washed with water, dried over magnesium sulfate and evaporated to give a residue, which was then dissolved in 23 ml of toluene. To the mixture was added 145 mg of p-toluenesulfonic acid, which was refluxed for 1.5 hours. The solvent was removed under reduced pressure to give a residue, which was dissolved in 13 ml of THF and stirred under ice-cooling. To the reaction mixture was added 1 ml of a THF solution of 2.0M tetra-n-butylammonium fluoride, which was stirred for 10 minutes. The reaction mixture was poured into ice-water containing sodium bicarbonate and extracted with dichloromethane. The dichloromethane layer was washed with an aq. sodium bicarbonate and water, dried over magnesium sulfate and evaporated to give a residue, which was then chromatographed on silica gel (toluene/ethyl acetate=9/1) and lyophilized from benzene to give 270 mg of the objective compound (Id-3) in 29% yield.

후처리

  1. stirringstirred for 2 hours
  2. extractionextracted with dichloromethane
  3. washThe dichloromethane layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a residue, which
  7. temperaturewas refluxed for 1.5 hours
  8. customThe solvent was removed under reduced pressure
  9. customto give a residue, which
  10. stirringstirred under ice-
  11. temperaturecooling
  12. stirringwas stirred for 10 minutes
  13. extractionextracted with dichloromethane
  14. washThe dichloromethane layer was washed with an aq. sodium bicarbonate and water
  15. dry with materialdried over magnesium sulfate
  16. customevaporated
  17. customto give a residue, which
  18. customwas then chromatographed on silica gel (toluene/ethyl acetate=9/1)

출처 및 근거

ORD 기록
ord-64a09ea974ea4b29b1aceaaf796a81ab
출처 데이터셋
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05319099

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트