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Imidazole → (S)-1,3-Di-[(tert-butyldimethylsilyloxy)]-4-methyl-4-pentene

HRID 1740483
Notes
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Reaction equation

HRID 1740483 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[Si:9]([O:16][CH2:17][CH2:18][C@H:19]([OH:23])[C:20]([CH3:22])=[CH2:21])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1.OS([O-])(=O)=O.[K+]>CN(C=O)C>[Si:9]([O:16][CH2:17][CH2:18][C@H:19]([O:23][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7])[C:20]([CH3:22])=[CH2:21])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516920Potassium bisulfateHCID 10966327(S)-1-[(tert-butyldimethylsilyloxy)]-4-methyl-4-penten-3-ol

Product 1

HCID 11336893(S)-1,3-Di-[(tert-butyldimethylsilyloxy)]-4-methyl-4-penteneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

946 mg (6.28 mmol, 1.3 equivalents) of tert-butyldimethylchlorosilane is added to a solution of 1.173 g (4.83 mmol) of (S)-1-[(tert-butyldimethylsilyloxy)]-4-methyl-4-penten-3-ol 10 and 855 mg (12.56 mmol, 2.6 equivalents) of imidazole in 15.0 ml of absolute DMF. The mixture is stirred for 16 hours at room temperature. It is mixed with 50 ml of an aqueous 1 M KHSO4 solution and extracted four times with 50 ml of Et2O each. The combined ether extracts are dried on MgSO4. After the solvent is distilled off in a vacuum, the residue is flash-chromatographed by a silica gel column with pentane/Et2O (20:1). As an alternative to this aqueous working-up, the reaction mixture can be chromatographed directly. By the two variations of working-up procedure, 1.643 g (4.73 mmol, 98%) of 11 is obtained.

Workup

  1. extractionextracted four times with 50 ml of Et2O each
  2. dry with materialThe combined ether extracts are dried on MgSO4
  3. distillationAfter the solvent is distilled off in a vacuum
  4. customthe residue is flash-chromatographed by a silica gel column with pentane/Et2O (20:1)
  5. customAs an alternative to this aqueous working-up, the reaction mixture can be chromatographed directly

Sources & evidence

ORD record
ord-ccd9ee943c194607a49c7221f04ea0df
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05969145

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes