HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

p-Toluenesulfonic acid → HCID 54114972, compound

HRID 1109365
Notes
Print preview

Reaction equation

HRID 1109365 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

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

Product 1

HCID 54114972
HCID 54114972, compound
Yield 29%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-64a09ea974ea4b29b1aceaaf796a81ab
Source dataset
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05319099

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes