Imidazole → HCID 87542336, compound

HRID 388737Notes

Reaction equation

HRID 388737 reaction equation
[Si:1]([O:18][C@H:19]1[C@@:25]2([CH3:26])[C@H:23]([O:24]2)[CH2:22][C@@H:21]([OH:27])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.Cl[Si:34]([CH2:39][CH3:40])([CH2:37][CH3:38])[CH2:35][CH3:36]>CN(C)C=O.O>[C:14]([Si:1]([O:18][C@@H:19]1[CH2:20][C@H:21]([O:27][Si:34]([CH2:39][CH3:40])([CH2:37][CH3:38])[CH2:35][CH3:36])[CH2:22][C@@H:23]2[C@@:25]1([CH3:26])[O:24]2)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 87628157HCID 87628157, compound

Product 1

HCID 87542336HCID 87542336, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound of Example 13B (16.0 g, 42 mmol) was dissolved in 20 mL of dimethylformamide; 7.1 g of imidazole (100 mmol, 2.5 equivalents) was added, followed by 10.5 mL of chlorotriethylsilane. The resultant mixture was stirred overnight at ambient temperature, then was diluted with water and extracted with ethyl acetate. The organic phase was concentrated washed with brine and dried over Na2SO4. After concentrating in vacuo, the residue was purified by flash chromatography, eluting with a gradient from 50% to 100% dichloromethane in hexanes to provide the titled compound (14.0 g, 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic phase was concentrated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentrating in vacuo
  6. customthe residue was purified by flash chromatography
  7. washeluting with a gradient from 50% to 100% dichloromethane in hexanes

Sources & evidence

ORD record
ord-04d6935ce25a48bebff43a551d52a15c
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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