Imidazole → 1-(t-Butyldimethylsilyl)oxymethyl-4-methoxymethoxy-5-methylnaphthalene

HRID 488120Notes

Reaction equation

HRID 488120 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[OH:9][CH2:10][C:11]1[C:20]2[C:15](=[C:16]([CH3:21])[CH:17]=[CH:18][CH:19]=2)[C:14]([O:22][CH2:23][O:24][CH3:25])=[CH:13][CH:12]=1.N1C=CN=C1>CN(C)C1C=CN=CC=1.O>[Si:5]([O:9][CH2:10][C:11]1[C:20]2[C:15](=[C:16]([CH3:21])[CH:17]=[CH:18][CH:19]=2)[C:14]([O:22][CH2:23][O:24][CH3:25])=[CH:13][CH:12]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 149864541-Hydroxymethyl-4-methoxymethoxy-5-methylnaphthalene

Product 1

HCID 149864551-(t-Butyldimethylsilyl)oxymethyl-4-methoxymethoxy-5-methylnaphthaleneYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

13.7 g of t-butylchlorodimethylsilane was added to an N,N-dimethylaminopyridine (100 ml) solution of 14 g of 1-hydroxymethyl-4-methoxymethoxy-5-methylnaphthalene,6.64 g of imidazole, and 0.4 g of 4-dimethylaminopyridine and agitated at room temperature overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate. Thereafter, the resultant organic phase was washed with water and then with a saturated saline solution. After drying with anhydrous magnesium sulfate, the solvent was distilled off and the residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to obtain 19 g of the captioned compound as a light brown oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThereafter, the resultant organic phase was washed with water
  3. dry with materialAfter drying with anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-47477dfd1ee04e73b9e2ebf4599fe68f
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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