tert-Butyldimethylsilyl chloride → HCID 69212167, compound

HRID 2252045Notes

Reaction equation

HRID 2252045 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]2[CH2:19][OH:20])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]2[CH2:19][O:20][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 17981653HCID 17981653, compound

Product 1

HCID 69212167HCID 69212167, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of 1-(4-methoxybenzyl)-2-hydroxymethyl-4-phenylimidazole (1.68 g, 5.71 mmol) in CH2Cl2 (35 mL) with N,N-diisopropylethylamine (3.2 mL, 18.4 mmol) and tert-butyldimethylsilyl chloride (TBSCl) (1.46 g, 9.69 mmol) at room temperature for 60 hours. Quench with H2O (40 mL), extract with CH2Cl2 (100 mL), dry (Na2SO4), and concentrate in vacuo. Purify the residue by flash chromatography (SiO2, hexane/EtOAc 20:1→9:1) to provide 2.09 g (90% yield). MS (ES+): m/z=409 (M+H)+

Workup

  1. customQuench with H2O (40 mL)
  2. extractionextract with CH2Cl2 (100 mL)
  3. dry with materialdry (Na2SO4)
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by flash chromatography (SiO2, hexane/EtOAc 20:1→9:1)
  6. customto provide 2.09 g (90% yield)

Sources & evidence

ORD record
ord-a1a958105be54dd7a2f0b39d9d5add7c
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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