Imidazole → Tert-butyl(3-methoxy-4-nitrobenzyloxy)dimethylsilane

HRID 576450Notes

Reaction equation

HRID 576450 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:6][OH:7].N1C=CN=C1.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20]>ClCCl>[C:19]([Si:23]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:26])[CH3:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 6029613-Methoxy-4-nitrobenzyl alcohol

Product 1

HCID 66664343Tert-butyl(3-methoxy-4-nitrobenzyloxy)dimethylsilaneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxy-4-nitrobenzyl alcohol (2.15 g, 11.75 mmol) and imidazole (880 mg, 12.94 mmol) in dry dichloromethane (58 ml) at 0° C. was quickly added tert-butyldimethylchlorosilane in one portion and the mixture was stirred at for 1 hour. LC-MS analysis indicated complete conversion. The solution was washed with ice cold water (50 ml) dried over Na2SO4, adsorbed on silicagel and purified by HPLC with hexanes/ethyl acetate 20-30% gradient to give compound 5 as a light yellow solid (3.3 g, 94%). MS (EI+): 282 (M-Me); 240 (M-tBu); H-NMR (400 MHz, CD2Cl2): 7.85 (1H, d, J=8 Hz) 7.19 (1H, s) 6.98 (1H, dq, J=8 Hz, 0.4 Hz) 4.82 (2H, s) 3.99 (3H, s) 1.0 (9H, s) 0.17 (6H, s). C-NMR (400 MHz, CD2Cl2): 153.96, 150.05, 138.73, 126.32, 117.74, 111.26, 64.65, 57.06, 26.30, 18.90, −4.97.

Workup

  1. customat 0° C.
  2. washThe solution was washed with ice cold water (50 ml)
  3. dry with materialdried over Na2SO4
  4. custompurified by HPLC with hexanes/ethyl acetate 20-30% gradient

Sources & evidence

ORD record
ord-288748e9b3c84781a9df1d935afcbd68
Source dataset
uspto-grants-2015_05
Patent number
US09040019B2

Reaction notes

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