Imidazole → HCID 178455454, compound

HRID 1364302Notes

Reaction equation

HRID 1364302 reaction equation
OC[C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.N1[CH:15]=[CH:14]N=C1.[CH3:16][C:17]([Si:20](Cl)(C)C)([CH3:19])[CH3:18].[OH2:24].[CH3:25]N(C=O)C>CC(=O)OCC>[C:17]([SiH2:20][O:24][C:14]([CH3:15])([CH3:25])[C@H:3]1[CH2:4][CH2:5][C@H:6]([CH2:9][OH:10])[CH2:7][CH2:8]1)([CH3:19])([CH3:18])[CH3:16]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178520956HCID 178520956, compound

Product 1

HCID 178455454HCID 178455454, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-(4-hydroxymethyl-cyclohexyl)-methanol (50 g, 347 mmol) in DMF (700 mL) at rt was added sequentially imidazole (47.2 g, 693 mmol) and TBDMSCl (44.3 g, 294 mmol). The mixture was poured into water and the product extracted with ether. The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. Chromatography over SiO2 (Hex/EA 4:1, 2:1) gave the desired mono-protected compound as a colourless oil (40.1 g, 45% yield).

Workup

  1. extractionthe product extracted with ether
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-376e3925d9af498f8d857ffda9b97362
Source dataset
uspto-grants-2011_02
Patent number
US07888359B2

Reaction notes

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