Imidazole → 1-(Chloroacetamido)-7-(tert-butyldiphenylsilyoxy)naphthalene

HRID 1862008Notes

Reaction equation

HRID 1862008 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:16])[CH:14]=2)[CH:9]=[CH:8][CH:7]=1)=[O:4].[C:17]([Si:21]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)Cl)([CH3:20])([CH3:19])[CH3:18].N1C=CN=C1.CCOC(C)=O>CN(C=O)C>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:14]=2)[CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 94078tert-ButyldiphenylchlorosilaneHCID 186212152-chloro-N-(7-hydroxynaphthalen-1-yl)acetamide

Product 1

HCID 700098281-(Chloroacetamido)-7-(tert-butyldiphenylsilyoxy)naphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of product from Step H (13.6 g, 57.87 mmol), tert-butyldiphenylchlorosilane (14.86 mL, 69.45 mmol), and imidazole (5.9 g, 86.8 mmol) in DMF (250 mL) was stirred at room temperature for 72 hours. The reaction was poured into EtOAc (200 mL), and washed with H2O (3×100 mL). The organic layer was dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (15% ethyl acetate/hexane) to provide the title compound as a brown solid.

Workup

  1. washwashed with H2O (3×100 mL)
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-df263db1cfcf466aa9ead562a78bb154
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

Loading…