Imidazole → HCID 59545204, compound

HRID 1960102Notes

Reaction equation

HRID 1960102 reaction equation
CN(C=O)C.[OH:6][C@@H:7]([CH2:14]/[CH:15]=[C:16](/[CH3:20])\[CH2:17][CH:18]=[CH2:19])[C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9].[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>C(OCC)C.C(OCC)(=O)C>[C:24]([Si:21]([CH3:23])([CH3:22])[O:6][C@@H:7]([CH2:14]/[CH:15]=[C:16](/[CH3:20])\[CH2:17][CH:18]=[CH2:19])[C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 45258939HCID 45258939, compound

Product 1

HCID 59545204HCID 59545204, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an anhydrous DMF (250 mL) solution of the alcohol 4 (70.7 g, 329 mmol) was added tert-butyldimethylsilyl chloride (TBSCl, 55 g, 364 mmol) and imidazole (30 g, 441 mmol) at 0° C. The reaction was allowed to warm to room temperature, and was stirred overnight. The reaction progress was followed by TLC (5:1/hexanes:ethyl acetate). The reaction mixture was poured to a 4 L separation funnel containing diethyl ether (1.7 L), and was separated. The organics were washed with water (4×500 mL) and brine (1×250 mL), dried over magnesium sulfate. Filtration and evaporation under vacuum afforded the crude product 5 as yellowish oil (107 g, 99%), which was used directly for the next step without further purification.

Workup

  1. additionThe reaction mixture was poured to a 4 L separation funnel
  2. customwas separated
  3. washThe organics were washed with water (4×500 mL) and brine (1×250 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and evaporation under vacuum

Sources & evidence

ORD record
ord-df63060aee0e4efab9557e8386c888fa
Source dataset
uspto-grants-2013_04
Patent number
US08410305B2

Reaction notes

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