Imidazole → HCID 20517420, compound

HRID 2059138Notes

Reaction equation

HRID 2059138 reaction equation
N1C=CN=C1.[OH:6][CH:7]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9][CH2:8]1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C)C=O.CCOCC>[Si:16]([O:6][CH:7]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9][CH2:8]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 20517423HCID 20517423, compound

Product 1

HCID 20517420HCID 20517420, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Imidazole (2.45 g, 31.6 mmol) is added to a solution of (±) 5-hydroxy-2-methylcycloheptanone (2.03 g, 14.3 mmol) in dimethylformamide (35 ml) at 0° C. followed by t-butyldimethylsilyl chloride (2.38 g, 15.7 mmol) under nitrogen. The mixture is stirred at room temperature for 17 hours and then diluted with ether (100 ml) and washed three times with water. After drying (Na2SO4), the ether is removed in vacuo to afford (±) 5-t-butyldimethylsilyloxy-2-methylcycloheptanone (3.7 g, 100%). IR (neat)μ: 5.88 (C=O); NMR (CDCl3)δ: 0.1 (s, 6H, Si(CH3) 0.93 [s, 9H, Si(CH3)2 -C(CH3)3 ], 1.1 (d, J=2-CH3), 3.6-4.2 (m, 1H, 5-H).

Workup

  1. washwashed three times with water
  2. dry with materialAfter drying (Na2SO4)
  3. customthe ether is removed in vacuo

Sources & evidence

ORD record
ord-2d93d67389e4414fbb7b6aaf174349a9
Source dataset
uspto-grants-1982_03
Patent number
US04322357

Reaction notes

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