Imidazole → HCID 23518554, compound

HRID 1836871Notes

Reaction equation

HRID 1836871 reaction equation
[Br:1][C:2]1[C:11]([CH2:12][CH2:13][CH2:14][OH:15])=[CH:10][C:9]2[C:8]([CH3:17])([CH3:16])[CH2:7][CH2:6][C:5]([CH3:19])([CH3:18])[C:4]=2[CH:3]=1.N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C)C=O.C(OCC)C>[Br:1][C:2]1[C:11]([CH2:12][CH2:13][CH2:14][O:15][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:10][C:9]2[C:8]([CH3:17])([CH3:16])[CH2:7][CH2:6][C:5]([CH3:19])([CH3:18])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 23498867HCID 23498867, compound

Product 1

HCID 23518554HCID 23518554, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 10.2 g (31.55 mmol) of 2-bromo-3-(3-hydroxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene in 80 mL of dimethlformamide was added 9.46 g (138.8 mmol) of imidazole and 10.46 g (69.4 mmol) of tert-butyldimethylsilyl chloride. After 4 hours the reaction mixture was diluted with diethyl ether and washed with 1 N aqueous ammonium chloride and brine. The organic fraction was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (gradient elution: 1-2% ethyl acetate/hexane) to afford 9.17 g (66%) of 2-bromo-3-(3-t-butyldimethylsiloxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene.

Workup

  1. washwashed with 1 N aqueous ammonium chloride and brine
  2. dry with materialThe organic fraction was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel (gradient elution: 1-2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8053d3d285a94920a820463d0886d86c
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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