Imidazole → (3S)-3-(tert-Butyldimethylsiloxy)-3-cyclohexylprop-1-yne

HRID 648672Notes

Reaction equation

HRID 648672 reaction equation
N1[CH:5]=[CH:4]N=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].O.[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].CN(C)[CH:23]=[O:24]>>[Si:10]([O:24][C@@H:23]([CH:17]1[CH2:16][CH2:15][CH2:20][CH2:19][CH2:18]1)[C:4]#[CH:5])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 6228DimethylformamideHCID 8058HexaneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11983898(3S)-3-(tert-Butyldimethylsiloxy)-3-cyclohexylprop-1-yne

Procedure

To a solution of (S)-3-cyclohexylprop-1-yn-3-ol, (obtained according to Preparation 10) (2.76 g, 0.02 mol), in 10 ml N,N-dimethylformamide (DMF), cooled to 0° C., was added imidazole (2.1 g), followed by tert-butyldimethylchlorosilane (3.1 g, 0.02 mol). The mixture was stirred for 3 h. Water (80 ml) and hexane (80 ml) were added; the organic layer was separated and combined with 2×80 ml of hexane extractions of the aqueous layer. The solvent was removed (in vacuo), after drying over sodium sulfate, to give a crude residue (4.3 g) which was chromatographed on silica gel (80 g), eluting with ethyl acetate-hexane (2:1, v/v) to afford (S)-3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-yne.

Workup

  1. customthe organic layer was separated
  2. extractioncombined with 2×80 ml of hexane extractions of the aqueous layer
  3. customThe solvent was removed (in vacuo)
  4. dry with materialafter drying over sodium sulfate
  5. customto give a crude residue (4.3 g) which
  6. customwas chromatographed on silica gel (80 g)
  7. washeluting with ethyl acetate-hexane (2:1, v/v)

Sources & evidence

ORD record
ord-cce85f4917e848c489e972ae28d5ec41
Source dataset
uspto-grants-1988_04
Patent number
US04735966

Reaction notes

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