Imidazole → HCID 67609918, compound

HRID 1847105Notes

Reaction equation

HRID 1847105 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][CH2:16]/[C:17](=[CH:18]\[CH:19]=[C:20]3\[CH2:21][C@@H:22]([OH:27])[CH2:23][CH2:24][C:25]\3=[CH2:26])/[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].N1C=CN=C1.Cl[Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH2:36][CH3:37].[Cl-].[NH4+]>ClCCl>[CH2:36]([Si:35]([CH2:40][CH3:41])([CH2:38][CH3:39])[O:27][CH:22]1[CH2:23][CH2:24][C@@:25]2([CH3:26])[C:20](=[CH:19][CH:18]=[C:17]3[C@@H:16]2[CH2:15][CH2:14][C@@:13]2([CH3:28])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8])[CH2:21]1)[CH3:37]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 25517Ammonium ChlorideHCID 5280795Vitamin D3

Product 1

HCID 67609918HCID 67609918, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available 7-dehydrocholesterol (10.6 g, 27.6 mmol) was dissolved in dichloromethane (90 mL), and then imidazole (3.75 g, 55.1 mmol) and chlorotriethylsilane (6.94 mL, 41.3 mmol) were added at room temperature, followed by stirring for 12 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with chloroform twice. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield a residue. The residue was purified by silica gel column chromatography to obtain the title compound (12.0 g, 87%).

Workup

  1. extractionfollowed by extraction with chloroform twice
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto yield a residue
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6dc86b002429403a83bbefc28fae957e
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

Loading…