Propylene Oxide → HCID 21193596, compound

HRID 1067722Notes

Reaction equation

HRID 1067722 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=[O:5])=[O:4].C([Li])CCC.CCCCCC.[CH2:30]1[O:33][CH:31]1[CH3:32].[NH4+].[Cl-]>C1COCC1.C(OCC)C>[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[C:10]([CH2:30][CH:31]([OH:33])[CH3:32])=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])(=[O:4])=[O:5]

Participants

8

Reactant 5

HCID 6378Propylene OxideHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 64202092-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 21193596HCID 21193596, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

5.426 g (18.7 mmol) of 1-(N,N-dimethylsulphamoyl)-2-tert-butyldimethylsilylimidazole are dissolved in 100 ml of freshly distilled THF under nitrogen and cooled to −78° C., and a solution of n-butyl-lithium in hexane (2.5M; 15 ml; 37.5 mmol) is added dropwise over a period of 10 min. The mixture is stirred for 30 min at −78° C. The solution is warmed to 0° C. with rapid stirring, and a solution of 3.0 ml (2.49 g; 42.9 mmol) of propylene oxide in 20 ml of freshly distilled THF is added dropwise over a period of 15 min. The mixture is stirred for 18 hours with heating at 20° C., and the mixture is then hydrolysed by adding 100 ml of saturated NH4Cl solution. The THF is removed under reduced pressure and the mixture obtained is extracted three times with 100 ml of dichloromethane. The organic layers are combined, dried (MgSO4) and evaporated under reduced pressure to yield an oil, which is subjected to column chromatography with diethyl ether as eluent to yield 1-(N,N-dimethylsulphamoyl)-2-tert-butyldimethylsilyl-5-(2-hydroxypropyl)imidazole in the form of a viscous yellow oil.

Workup

  1. temperatureThe solution is warmed to 0° C. with rapid stirring
  2. stirringThe mixture is stirred for 18 hours
  3. temperaturewith heating at 20° C.
  4. customThe THF is removed under reduced pressure
  5. customthe mixture obtained
  6. extractionis extracted three times with 100 ml of dichloromethane
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customto yield an oil, which

Sources & evidence

ORD record
ord-3e3dc3e129ef4b20a6c905647f393a7d
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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