Phosphorus oxychloride → 2-Tert-butyl-4-chloromethyl-5-methyl-oxazole

HRID 2215189Notes

Reaction equation

HRID 2215189 reaction equation
[C:1]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH3:11])[N+:9]=1[O-])([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:15]>C(Cl)Cl>[C:1]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH2:11][Cl:15])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 115718592-Tert-butyl-4,5-dimethyl-oxazole 3-oxide

Product 1

HCID 219495892-Tert-butyl-4-chloromethyl-5-methyl-oxazoleYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30 g of the above prepared 2-tert-butyl-4,5-dimethyl-oxazole 3-oxide (˜115 mmol) was dissolved in 390 ml of CH2Cl2 and treated dropwise with 12.74 ml of POCl3 (139 mmol). The reaction mixture was refluxed over night and then quenched by carefully pouring onto crashed ice/3N NaOH. Separation of the layers, additional extraction of the aqueous phase with CH2Cl2, drying of the combined organic phase over sodium sulfate, evaporation of the solvents, and, finally, flash chromatography (SiO2, hexane/AcOEt=85/15) yielded 16.29 g of the title compound as white crystals of mp. 41–44°.

Workup

  1. temperatureThe reaction mixture was refluxed over night
  2. customquenched
  3. additionby carefully pouring
  4. customSeparation of the layers, additional extraction of the aqueous phase with CH2Cl2
  5. dry with materialdrying of the combined organic phase over sodium sulfate, evaporation of the solvents

Sources & evidence

ORD record
ord-bae85242aeb44f7a9b36addc016e1b4c
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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