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Imidazole → 1-t-BUTYLDIMETHYLSILYLOXY-2,3-DIMERCAPTOPROPANE

HRID 636870
Notes
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Reaction equation

HRID 636870 reaction equation
[SH:1][CH:2]([CH2:5][SH:6])[CH2:3][OH:4].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Cl-].[NH4+]>C1COCC1>[Si:12]([O:4][CH2:3][CH:2]([SH:1])[CH2:5][SH:6])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3080DimercaprolHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 212558391-t-BUTYLDIMETHYLSILYLOXY-2,3-DIMERCAPTOPROPANEYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,3-dimercapto-1-propanol (15.0 ml, 150 mmol) and imidazole (15.3 g, 224 mmol, 1.5 eq) in THF (300 mL) was added t-butyldimethylsilyl chloride (21.4 g, 142 mmol, 0.95 eq) at 0° C. The mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. A saturated solution of ammonium chloride was added and the aqueous phase was extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulphate and the solvent was evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (90:10) to give the pure compound (32.04 g) in 94.5w yield.

Workup

  1. extractionthe aqueous phase was extracted with dichloromethane
  2. dry with materialThe organic layer was dried with anhydrous sodium sulphate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude material was purified by flash chromatography with a mixture of hexane and ethyl acetate (90:10)

Sources & evidence

ORD record
ord-f94a4f2c8e674a8e87017adc7c2f075e
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06194576B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes