Benzaldehyde → HCID 58951927, compound

HRID 1694786Notes

Reaction equation

HRID 1694786 reaction equation
[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=[O:5])=[O:4].C([Li])CCC.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[CH:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.CCCCCC>[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[C:9]([CH:25]([OH:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]=[C:7]1[Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])(=[O:4])=[O:5]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 28928tert-Butyldimethylsilyl chlorideHCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium2×

Product 1

HCID 58951927HCID 58951927, compoundYield 107.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of 0.30 g (1.71 mmol) 1-(dimethylsulfamoyl)-imidazole in 10 ml tetrahydrofuran were added 1.2 ml (1.88 mmol) of a 1.6M butyl lithium solution in hexane at −75° C. After stirring for 15 min 0.30 g (2 mmol) tert-butyldimethylsilyl chloride was added at −75° C. and the mixture was stirred at ambient temperature for 2 h. The mixture was cooled down again to −75° C. and 1.2 ml (1.88 mmol) of a 1.6M butyl lithium solution in hexane were added. After stirring for 30 min 0.22 ml (2.14 mmol) benzaldehyde was added at −75° C. and the mixture was allowed to reach room temperature overnight. The mixture was partitioned between water and dichloromethane, re-extracted with dichloromethane and the combined organic layers are dried over MgSO4, filtered and evaporated to yield 0.73 g of an yellow oil, that was used directly in the next step, MS (EI): 338.1 ((M-tBu)+.).

Workup

  1. additionwas added at −75° C.
  2. temperatureThe mixture was cooled down again to −75° C.
  3. additionwas added at −75° C.
  4. waitto reach room temperature overnight
  5. customThe mixture was partitioned between water and dichloromethane
  6. extractionre-extracted with dichloromethane
  7. dry with materialthe combined organic layers are dried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-0669a9c9eb4a4f52a799e7147d053ce7
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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