Imidazole → HCID 57912293, compound

HRID 1499327Notes

Reaction equation

HRID 1499327 reaction equation
[N+:1]([C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:12][OH:13])([O-:3])=[O:2].CN(C=O)C.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(OCC)(=O)C>[Si:24]([O:13][CH2:12][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:9]([CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 13519807[3-(hydroxymethyl)-2-nitrophenyl]methanol

Product 1

HCID 57912293HCID 57912293, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a clean, dry round-bottom flask was added 2-nitro-1,3-benzenedimethanol (818 mg, 4.47 mmol), anhydrous DMF (40 mL), and imidazole (304.2 mg, 4.47 mmol). The solution was maintained at 0° C. while tert-butyldimethylsilylchloride (337 mg, 2.24 mmol) was slowly added. The resulting pale yellow solution was allowed to warm to room temperature and stirred overnight under argon before being diluted with ethyl acetate (100 mL), washed with water (5×50 mL), dried over MgSO4, filtered, concentrated on a rotary evaporator, and purified by silica gel chromatography (30% EtOAc:hexanes) to yield 3-(tert-butyldimethylsilyloxymethyl)-2-nitro-hydroxymethylbenzene as a yellow oil which crystallized upon further solvent removal in vacuo. The excess 2-nitro-1,3-benzenedimethanol was recovered and re-subjected to the reaction conditions to yield Compound 9 in 80% yield after three iterations.

Workup

  1. additionwas slowly added
  2. washwashed with water (5×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. custompurified by silica gel chromatography (30% EtOAc:hexanes)

Sources & evidence

ORD record
ord-14c4f85fed8e4a51830a91076a8a750d
Source dataset
uspto-grants-2015_12
Patent number
US09200097B2

Reaction notes

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