Imidazole → HCID 178455305, compound

HRID 402542Notes

Reaction equation

HRID 402542 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[C@H:14]1([OH:23])[CH2:21][CH2:20][CH2:19][C@@H:18]([OH:22])[CH2:17][CH2:16][CH2:15]1>CN(C1C=CN=CC=1)C.C1COCC1>[C:9]([Si:6]([CH3:8])([CH3:7])[O:22][C@@H:18]1[CH2:19][CH2:20][CH2:21][C@H:14]([OH:23])[CH2:15][CH2:16][CH2:17]1)([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178521540HCID 178521540, compound

Product 1

HCID 178455305HCID 178455305, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

21.4 g (312 mmol) of imidazole, 34.5 g (229 mmol) of t-butyldimethylsilyl chloride and 10 mg of DMAP were added to a solution of cis-1,5-cyclooctanediol in 500 mL of THF. The reaction mixture was stirred for 2 h before quenching with water followed by extraction with ethyl acetate. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. Filtration and evaporation under reduced pressure gave crude product which was purified by silica gel chromatography (n-heptane/ethyl acetate, 4:1) to give 26.0 g of the desired product as a colourless oil. Rt=3.00 min (Method J). Detected mass: 259.2 (M+H+).

Workup

  1. custombefore quenching with water
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and evaporation under reduced pressure
  6. customgave crude product which
  7. customwas purified by silica gel chromatography (n-heptane/ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-cf31ef48aec746b990ad2b05a7f02c06
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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