Imidazole → HCID 87775793, compound

HRID 132522Notes

Reaction equation

HRID 132522 reaction equation
[C:1]([CH:7]([OH:13])[CH2:8][CH:9]([OH:12])[CH2:10][OH:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl.O>[Si:19]([CH:10]([OH:11])[CH:9]([OH:12])[CH2:8][CH:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[OH:13])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 87775794HCID 87775794, compound

Product 1

HCID 87775793HCID 87775793, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 (70 g, 0.368 mol) in CH2Cl2 (2.0 L) is added imidazole (31.3 g, 0.46 mol) and tert-butyldimethylsilyl chloride (58.2 g, 0.386 mol) and stirred at room temperature for 3 h. The reaction mixture is diluted with water, the organic layer separated and washed with water and brine and then dried over MgSO4. After filtration, the filtrate is concentrated and the residue is purified on a silica gel column using ethyl acetate:hexanes as eluent to give 91.2 g (81%) of product as an oil: 1H NMR (DMSO-d6): δ 4.66 (d, J=5.2 Hz, 1H), 4.14-3.90 (m, 2H), 3.54-3.25 (m, 3H), 1.84-1.72 (m, 1H), 1.51-1.39 (m, 1H), 1.10 (s, 9H), 0.83 (s, 9H), 0.01 (s, 6H).

Workup

  1. customthe organic layer separated
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated
  6. customthe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-4026e6f651144bb284250b5d55824797
Source dataset
uspto-grants-2008_06
Patent number
US07388002B2

Reaction notes

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