Imidazole → 130745-64-1

HRID 870486Notes

Reaction equation

HRID 870486 reaction equation
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.N1C=CN=C1.[C:14]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15]>O1CCOCC1>[Si:18]([O:7][CH:4]1[CH2:5][CH2:6][CH:1]([OH:8])[CH2:2][CH2:3]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 111621,4-CyclohexanediolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 15632834130745-64-1Yield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
15 °C

Procedure

Into a 1000-mL 3-necked round-bottom flask was placed cyclohexane-1,4-diol (20 g, 172.18 mmol, 1.00 equiv), 1,4-dioxane (500 mL) and 1H-imidazole (17.58 g, 258.24 mmol, 1.50 equiv). This was followed by the addition of a solution of tert-butyl(chloro)diphenylsilane (49.69 g, 180.78 mmol, 1.05 equiv) in dioxane (100 mL) dropwise with stirring at 15° C. The resulting solution was stirred for 15 h at 15-20° C. The solids were filtered out. The filtrate was diluted with 200 mL of water. The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0:1-1:60-1:50-1:30-1:20). Purification afforded 32.98 g (54%) of 4-[(tert-butyldiphenylsilyl)oxy]cyclohexan-1-ol (74.1) as a white semi-solid.

Workup

  1. customInto a 1000-mL 3-necked round-bottom flask was placed
  2. stirringThe resulting solution was stirred for 15 h at 15-20° C
  3. filtrationThe solids were filtered out
  4. additionThe filtrate was diluted with 200 mL of water
  5. extractionThe resulting solution was extracted with 3×200 mL of ethyl acetate
  6. concentrationconcentrated under vacuum
  7. customPurification

Sources & evidence

ORD record
ord-209d2b4d743140bb9109f1987b38381a
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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