Hydrochloric Acid → HCID 18003482, compound

HRID 479150Notes

Reaction equation

HRID 479150 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=1.Cl[CH:24]([O:26]C)Cl.Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:22][C:18]1[CH:17]=[C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])[CH:21]=[CH:20][C:19]=1[CH:24]=[O:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 18003553HCID 18003553, compound

Product 1

HCID 18003482HCID 18003482, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 6.00 g of 5-methyl-2-phenyl-4-(2-m-tolyloxy-ethyl)-oxazole and 4.70 g of dichloromethylmethylether in 30 ml of CH2Cl2 was treated at 0° C. with 11.2 ml TiCl4 over 15 min and stirring was continued at 0° C. for 2.5 h. The red solution was treated at 0° with 600 ml of 1 N aqueous HCl, the organic layer was washed with 0.1 N aqueous NaOH and twice with brine. The organic layer was dried, the solvent evaporated and the residue was chromatographed on silica (n-hexane/AcOEt, 7:1) to give 3.42 g (52%) of the title compound as a pale yellow solid.

Workup

  1. washthe organic layer was washed with 0.1 N aqueous NaOH and twice with brine
  2. customThe organic layer was dried
  3. customthe solvent evaporated
  4. customthe residue was chromatographed on silica (n-hexane/AcOEt, 7:1)

Sources & evidence

ORD record
ord-da98955bd33648fca640d0cf09a4131a
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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