Imidazole → 1-(2-Chloro-6-fluorophenyl)ethyl (t-butyldimethylsilyl)ether

HRID 266586Notes

Reaction equation

HRID 266586 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([OH:11])[CH3:10].N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([O:11][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH3:10]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 133042791-(2-Chloro-6-fluorophenyl)ethan-1-ol

Product 1

HCID 538837541-(2-Chloro-6-fluorophenyl)ethyl (t-butyldimethylsilyl)etherYield 94.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

1-(2-Chloro-6-fluorophenyl)ethanol (8.5 g), imidazole (8.1 g) and t-butyldimethylsilylchloride (8.71 g) were stirred in DMF for 24 hours. The mixture was diluted with ether and washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 1-(2-chloro-6-fluorophenyl)ethyl (t-butyldimethylsilyi)ether (13.3 g) as a clear oil, NMR (CDCl3) -0.1(s,3H), 0.05(s,3H), 0.85(s,9H), 1.5(d,3H), 5.4(q, 1H), 6.9(m, 1H), 7.05(m,2H).

Workup

  1. washwashed with water
  2. dry with materialdried (anhydrous magnesium sulphate)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-0d0da5bfb77545149d435d1af9e8ba8b
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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