Imidazole → tert-Butyl-dimethyl-(3-nitro-benzyloxy)-silane

HRID 547586

Reaction equation

HRID 547586 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][OH:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].N1C=CN=C1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl>[C:18]([Si:21]([CH3:23])([CH3:22])[O:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:20])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 692673-Nitrobenzyl alcohol

Product 1

HCID 59428294tert-Butyl-dimethyl-(3-nitro-benzyloxy)-silaneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of compound 2 (4.7 g, 0.03 mol) and imidazole (2.71 g, 0.04 mol) in dry CH2Cl2 (30 mL) under N2 atmosphere at 0° C. was added a solution of TBDMS-Cl (5.08 g, 0.033 mol) in CH2Cl2 (15 mL) and allowed to stir at room temperature for 2 h. The precipitated solid was isolated by filtration and washed with CH2Cl2 (5×20 mL). The filtrate and combined CH2Cl2 fractions were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude mass was purified by column chromatography (silica gel, eluant=3:7 mixture of ethyl acetate and hexane) to afford compound 3 (7.2 g, 90%) as a liquid.

Workup

  1. customThe precipitated solid was isolated by filtration
  2. washwashed with CH2Cl2 (5×20 mL)
  3. dry with materialwere dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mass was purified by column chromatography (silica gel, eluant=3:7 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-511748dbc83f4448af15c5ea3b65b0a4
Source dataset
uspto-grants-2011_05
Patent number
US07939556B2

Linked notes

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