Imidazole → HCID 69304890, compound

HRID 132528Notes

Reaction equation

HRID 132528 reaction equation
[C:1]([CH:7]([OH:14])[CH2:8][CH:9]([OH:13])[CH2:10][CH2:11][OH:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].N1C=CN=C1.[Si:20](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[Si:20]([CH:11]([OH:12])[CH2:10][CH:9]([OH:13])[CH2:8][CH:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[OH:14])([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 87775813HCID 87775813, compound

Product 1

HCID 69304890HCID 69304890, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 59 (8.0 g, 39.16) and imidazole (3.0 g, 43.07 mmol) in CH2Cl2 (170 mL) is added TBDPS-chloride (11.20 mL, 39.16 mmol) over a period of 1 h at room temperature. After stirring for 1 more h, the solvent is removed and the residue is purified on a silica gel column using ethyl acetate:hexanes as eluent to provide 13 g (75%) of 60, as a colorless oil: 1HNMR (DMSO-d6): 7.57-7.67 (m, 4 H), 7.36-7.47 (m, 6 H), 4.55 (d, J=5.8 Hz, 1 H), 4.06-4.11 (m, 2 H), 3.66-3.85 (m, 3 H), 1.53-1.73 (m, 4 H), 1.11 (s, 9 H) and 0.97 (s, 9 H). IR (KBr, cm−1): 3514, 2959, 2858, 1726, 1473 and 1428. HRMS Calcd for C26H38O4Si (M+H)+ 443.2617. Found 443.2598.

Workup

  1. customthe solvent is removed
  2. customthe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-a7768acb77524d9a80701ab061db54e5
Source dataset
uspto-grants-2008_06
Patent number
US07388002B2

Reaction notes

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