Imidazole → HCID 178455316, compound

HRID 1774390Notes

Reaction equation

HRID 1774390 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCCCCC.C(OCC)(=O)C>CN(C)C=O.O.CCCCCC>[CH2:1]([O:8][C:9]([CH2:11][C@H:12]1[CH2:13][CH2:14][C@H:15]([O:18][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:16][CH2:17]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21226206Ethyl acetate hexaneHCID 178520752HCID 178520752, compound

Product 1

HCID 178455316HCID 178455316, compoundYield 92.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of trans-4-benzyloxycarbonylmethyl-1-hydroxycyclohexane (2.20 g, 8.86 mmol) in dimethylformamide (31 mL) were added imidazole (953 mg, 14.0 mmol) and t-butyldimethylsilyl chloride (1.60 g, 10.6 mmol) at room temperature, and the mixture was stirred at 60° C. for 3 h. The reaction mixture was diluted with water (70 mL) and hexane (200 mL) with stirring under ice cooling to separate the phases. The aqueous layer was extracted again with hexane, and the combined organic layer was concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 50:1) to give 2.96 g of trans-4-benzyloxycarbonylmethyl-1-t-butyldimethylsilyloxycyclohexane as oil (yield: 92%).

Workup

  1. stirringwith stirring under ice cooling
  2. customto separate the phases
  3. extractionThe aqueous layer was extracted again with hexane
  4. concentrationthe combined organic layer was concentrated under reduced pressure
  5. customthe residue thus obtained

Sources & evidence

ORD record
ord-0df04006899e413fa5461c717477cdbb
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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