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

HRID 1288774Notes

Reaction equation

HRID 1288774 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-butyldimethylsilyl)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-51cb453fdecb42e2a640b2b044ed91ff
Source dataset
uspto-grants-1998_05
Patent number
US05747424

Reaction notes

Loading…