Imidazole → (R)-1-Cyclohexyl-1-phenyl-1-trimethylsiloxy-2-propanone

HRID 1087663Notes

Reaction equation

HRID 1087663 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].N1C=CN=C1.[CH:11]1([C@@:17]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](=[O:20])[CH3:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CCOCC>CN(C=O)C>[CH:21]1([C@:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([O:27][Si:2]([CH3:4])([CH3:3])[CH3:1])[C:18](=[O:20])[CH3:19])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 15030055(R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

Product 1

HCID 15105836(R)-1-Cyclohexyl-1-phenyl-1-trimethylsiloxy-2-propanoneYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 12 ml (95 mmoles) of trimethylsilyl chloride and 11.6 g (172 mmoles) of imidazole in 100 ml of DMF was added 20 g (86 mmoles) of (R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone. This mixture was heated to 85° C. overnight. The next day, the mixture was cooled and poured onto a mixture of 100 ml of petroleum ether and 100 ml of ether. This was extracted with water. The organic layer was separated, dried, and the solvent removed. The residue was chromatographed on silica gel with hexane as the eluent to give 18.0 g of clear oil. IR 2950, 1730 cm-1NMR (CDCl3) δ7.4(m, 5H), 2.3(t, 1H), 2.1(s, 3H), 1.9-1.0(m, 10H), 0.3(s, 9H).

Workup

  1. temperatureThe next day, the mixture was cooled
  2. extractionThis was extracted with water
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent removed
  6. customThe residue was chromatographed on silica gel with hexane as the eluent

Sources & evidence

ORD record
ord-1cbaa38756074c26b8232498e55e5dbe
Source dataset
uspto-grants-1991_07
Patent number
US05036107

Reaction notes

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