Imidazole → HCID 22125144, compound

HRID 1858273Notes

Reaction equation

HRID 1858273 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][OH:8])([O-:3])=[O:2].[C:12]([Si:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)Cl)([CH3:15])([CH3:14])[CH3:13].N1C=CN=C1>CN(C)C=O.CN(C)C1C=CN=CC=1>[Si:16]([O:8][CH2:7][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=[CH:10][CH:9]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 692673-Nitrobenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 22125144HCID 22125144, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5 g (33 mmol) of 3-nitrobenzyl alcohol in 100 ml of dimethylformamide was treated with 10.8 g (40 mmol) of tert-butyldiphenylchlorosilane, 6.7 g (99 mmol) of imidazole and 100 mg (0.9 mmol) of 4-(dimethylamino)pyridine and the mixture stirred at ambient temperature for 4 hours. The solvent was evaporated and the residue partitioned between 100 ml of ethyl acetate and 100 ml of 2M aqueous hydrochloric acid. The organic phase was washed with a further 50 ml of 2M aqueous hydrochloric acid, dried over magnesium sulfate, filtered and evaporated to afford 12.9 g (100%) of 3-(tert-butyldiphenylsilyloxymethyl)nitrobenzene as a colorless oil. [Mass spectrum (ESI) MH+ =392].

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between 100 ml of ethyl acetate and 100 ml of 2M aqueous hydrochloric acid
  3. washThe organic phase was washed with a further 50 ml of 2M aqueous hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a08e2ef26a2d4f0dbe4f4e9364b2c0fb
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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