Trimethylamine oxide → 2-Bromo-5-(2-pyrimidinyl)benzaldehyde

HRID 1956964ノート

反応式

HRID 1956964 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH2:14]Br.C[N+]([O-:20])(C)C>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH:14]=[O:20]

参加物

4

反応物 2

HCID 1145Trimethylamine oxideHCID 186631902-[4-Bromo-3-(bromomethyl)phenyl]pyrimidine

生成物 1

HCID 186631922-Bromo-5-(2-pyrimidinyl)benzaldehyde

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
55 °C

実験手順

To a solution of 1.75 g of the crude title compound of Step D in 6 mL of anhydrous dimethylsulfoxide ("DMSO") under argon, 3.0 g of anhydrous trimethylamine N-oxide (prepared as described in Soderquist et al., Tet. Letters., 27, 3961 (1986); this compound is also commercially available) were added and the mixture stirred at 55° C. for 12 hrs. The mixture was then cooled and added to 100 mL of ice/water and extracted with 3×50 mL of EtOAc. The combined organic extracts were washed once with 100 mL of brine and dried and evaporated. The residue was chromatographed on 100 mL of silica gel using Hexanes/EtOAc 6:1 to afford 0.86 g (81.5% for two steps) of the title compound of this step as a white solid.

後処理

  1. additionwere added
  2. temperatureThe mixture was then cooled
  3. extractionextracted with 3×50 mL of EtOAc
  4. washThe combined organic extracts were washed once with 100 mL of brine
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed on 100 mL of silica gel

出典と根拠

ORDレコード
ord-a3a3ecffda364657bf34d46f5f1333ab
出典データセット
uspto-grants-1998_07
特許番号
US05780473

反応ノート

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