Phosphorus oxychloride → 4-Chloromethyl-2-cyclohexyl-5-methyl-oxazole

HRID 2215204ノート

反応式

HRID 2215204 の反応式
[CH:1]1([C:7]2[O:8][C:9]([CH3:14])=[C:10]([CH3:13])[N+:11]=2[O-])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:17]>C(Cl)Cl>[Cl:17][CH2:13][C:10]1[N:11]=[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:8][C:9]=1[CH3:14]

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 219496082-Cyclohexyl-4,5-dimethyl-oxazole 3-oxide

生成物 1

HCID 219495724-Chloromethyl-2-cyclohexyl-5-methyl-oxazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

25.1 g of the above prepared 2-cyclohexyl-4,5-dimethyl-oxazole 3-oxide (˜88.8 mmol) was dissolved in 325 ml of CH2Cl2 and treated dropwise with 9.755 ml of POCl3 (1.2 eq.). 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, washing with Na2CO3 and water, drying of the combined organic phase over sodium sulfate, evaporation of the solvents, and, finally, flash chromatography (SiO2, hexane/AcOEt=9/1) afforded 4.12 g of the title compound as yellowish oil, exhibiting in the 1H-NMR the typical signal at 4.46 ppm (2H). The other, unstable regioisomer was not isolated.

後処理

  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. washwashing with Na2CO3 and water
  6. dry with materialdrying of the combined organic phase over sodium sulfate, evaporation of the solvents

出典と根拠

ORDレコード
ord-0fca3a66359c4f6db3781b00464ce35d
出典データセット
uspto-grants-2006_09
特許番号
US07109225B2

反応ノート

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