Imidazole → HCID 13305848, compound

HRID 1660045Notes

Reaction equation

HRID 1660045 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH3:14][CH2:15][CH2:16]CCC.C([O:22][CH2:23][CH3:24])C.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>[Cl-].[Na+].O.O>[Si:6]([O:25][CH2:26][CH2:27][C:28]1[CH:29]=[CH:16][CH:15]=[CH:14][C:24]=1[CH2:23][OH:22])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 8058HexaneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 13305848HCID 13305848, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 13.5 g of the reaction product of Part A in 50 ml of dry tetrahydrofuran under a nitrogen atmosphere is added with stirring 9.05 g of imidazole. The resulting solution is then cooled to -5° C. and 13.9 g of t-butyldimethylsilyl chloride is added. The resulting mixture is then maintained for 20 min and thereafter allowed to warm to ambient temperature. After 1 hr, the resulting mixture is then shaken with 500 ml of hexane and diethylether (2:1) and 250 ml of water and brine (1:1). The organic layer is then washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to yield a crude mixture of mono- and bis-silyl ethers corresponding to the starting material of Part A. This mixture of products is then chromatographed on 2 kg of silica gel, deactivated with 400 ml of ethyl acetate and eluted with 25% ethyl acetate and Skellysolve B to yield 6.82 g of formula XLIII product, o-(t-butyldimethylsilyloxyethyl)phenylmethanol. NMR absorptions are observed at 7.20-7.52, 4.57, 3.91 (t, J G.1), 2.93 (t, J 6.1), 0.82, and -0.08δ. Silica gel TLC Rf is 0.54 in 25% ethyl acetate and hexane.

Workup

  1. temperatureThe resulting mixture is then maintained for 20 min
  2. temperatureto warm to ambient temperature
  3. washThe organic layer is then washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield a crude
  7. additionThis mixture of products
  8. customis then chromatographed on 2 kg of silica gel
  9. washeluted with 25% ethyl acetate and Skellysolve B

Sources & evidence

ORD record
ord-5afdafa4e01f427cb42fda9c26cf73df
Source dataset
uspto-grants-1981_12
Patent number
US04306075

Reaction notes

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