Potassium Iodide → 1-[4-(4-{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole

HRID 1271391Notes

Reaction equation

HRID 1271391 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[O:6][CH:7]=1.[N:21]1([CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)[CH:25]=[CH:24][N:23]=[N:22]1.[I-].[K+].C[O-].[Na+]>CO>[F:18][C:17]([F:20])([F:19])[O:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]=[CH:8][C:5]2[O:6][CH:7]=[C:3]([CH2:2][O:36][C:33]3[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][CH2:27][CH2:26][N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)=[CH:31][CH:32]=3)[N:4]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 690715774-Chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole

Product 1

HCID 694744061-[4-(4-{2-[2-(4-Trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

MS: M=304.2(API+). 1H-NMR(400 MHz, D6-DMSO): δ=4.71(s, 2H, CH2Cl), 7.21(d, 1H, ═CH), 7.40(d, 2H, Ar—H), 7.58(d, 1H, ═CH), 7.87(d, 2H, Ar—H), 8.19(s, 1H, oxazole). 0.304 g (1.00 mmol) 4-Chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole, 0.217 g (1.00 mmol) 4-(4-[1,2,3]Triazol-1-yl-butyl)-phenol, 0.166 g (1.00 mmol) potassium iodide and 0.191 ml (1.00 mmol) of a 30% sodium methylate solution were added to 50.0 ml methanol and heated to reflux for 8 h. After removal of solvent, partitioning of the residue between 50 ml ethyl acetate and 15 ml water, the organic phase was washed with 10 ml water, 10 ml 0.1 N NaOH, 15 ml water twice and dried over sodium sulphate. The solution was concentrated until crystallisation of the product started. After leaving for 1 h at room temperature the precipitate was isolated, washed with ether and dried at 40° C. in vacuo. Yield 0.16 g (32%) 2, m.p. 138–140° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 h
  3. customAfter removal of solvent
  4. custompartitioning of the residue between 50 ml ethyl acetate and 15 ml water
  5. washthe organic phase was washed with 10 ml water, 10 ml 0.1 N NaOH, 15 ml water twice
  6. dry with materialdried over sodium sulphate
  7. concentrationThe solution was concentrated until crystallisation of the product
  8. customAfter leaving for 1 h at room temperature the precipitate
  9. customwas isolated
  10. washwashed with ether
  11. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-0b2c26536c9b4815be0970e2241c2aa4
Source dataset
uspto-grants-2007_04
Patent number
US07205325B2

Reaction notes

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