Imidazole → HCID 86597289, compound

HRID 2223335Notes

Reaction equation

HRID 2223335 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH2:44][C@@:42]2([CH3:43])[C@@H:38]([CH2:39][CH2:40][C@@H:41]2[OH:45])[C@@:37]2([CH:46]=[O:47])[C:28]=1[C:29]1[CH:30]=[CH:31][C:32]([O:48][CH3:49])=[CH:33][C:34]=1[CH2:35][CH2:36]2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH2:44][C@@:42]2([CH3:43])[C@@H:38]([CH2:39][CH2:40][C@@H:41]2[O:45][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[C@@:37]2([CH:46]=[O:47])[C:28]=1[C:29]1[CH:30]=[CH:31][C:32]([O:48][CH3:49])=[CH:33][C:34]=1[CH2:35][CH2:36]2)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 86597290HCID 86597290, compound

Product 1

HCID 86597289HCID 86597289, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.46 g of imidazole and 9.66 g of tert-butyldimethylsilyl chloride are added in succession at 0° C. to a solution of 12.49 g of alcohol 5 in 160 ml of N,N-dimethylformamide and stirred at room temperature until the reaction is completed. For working-up, the aqueous phase is mixed with water and extracted several times with diethyl ether. The combined organic phases are washed with water and saturated sodium chloride solution, dried on magnesium sulfate and concentrated by evaporation. The residue is purified by column chromatography (cyclohexane/ethyl acetate) and yields 14.36 g of silyl ether 6 as a yellow, viscous mass (GC-MS: m/z theor.: 602, pract.: 602).

Workup

  1. extractionextracted several times with diethyl ether
  2. washThe combined organic phases are washed with water and saturated sodium chloride solution
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is purified by column chromatography (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-32e7b1266b5041ec8e56351e3c1e1ce7
Source dataset
uspto-grants-2008_05
Patent number
US07375098B2

Reaction notes

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