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

HRID 703567Notes

Reaction equation

HRID 703567 reaction equation
[CH:1]1([C@H:7]([OH:10])[C:8]#[CH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].O>CN(C)C=O.CCCCCC>[Si:20]([O:10][C@@H:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:8]#[CH:9])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 10307864(S)-3-cyclohexyl-1-propyn-3-ol

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-3-cyclohexylprop-1-yn-3-ol, prepared as shown in Preparation 3 or 4, (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

Sources & evidence

ORD record
ord-e9f65862b7f744c683d580089b73eb13
Source dataset
uspto-grants-1991_01
Patent number
US04983627

Reaction notes

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