Tert-Butanesulfinamide → HCID 88924920、化合物

HRID 715057ノート

反応式

HRID 715057 の反応式
[O:1]1[C:5]([CH:6]=O)=[CH:4][N:3]=[CH:2]1.[CH3:8][C:9]([S:12]([NH2:14])=[O:13])([CH3:11])[CH3:10]>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[CH3:8][C:9]([S:12](/[N:14]=[CH:6]/[C:5]1[O:1][CH:2]=[N:3][CH:4]=1)=[O:13])([CH3:11])[CH3:10]

参加物

5

反応物 2

HCID 3382465Tert-ButanesulfinamideHCID 118293725-OXAZOLECARBOXALDEHYDE

生成物 1

HCID 88924920HCID 88924920、化合物収率 58.7%

試薬・触媒・溶媒 2

HCID 178477244HCID 178477244、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

Oxazole-5-carbaldehyde (1.0 g, 10.30 mmol), 2-methylpropane-2-sulfinamide (2.247 g, 18.54 mmol; CASRN 146374-27-8), and tetraethoxytitanium (8.460 g, 37.09 mmol) were stirred in THF (15 mL) and heated to 65° C. for 12 h under nitrogen. The reaction was cooled and poured onto water. The solids were filtered off and the filtrate was extracted with EtOAc. The layers were separated and the organic layer was dried (MgSO4), filtered and concentrated. The resulting residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (20 to 25% EtOAc) to afford 1.211 g (58.7%) of (E)-2-methyl-N-(oxazol-5-ylmethylene)propane-2-sulfinamide (20).

後処理

  1. temperatureThe reaction was cooled
  2. additionpoured onto water
  3. filtrationThe solids were filtered off
  4. extractionthe filtrate was extracted with EtOAc
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by SiO2 chromatography
  10. washeluting with an EtOAc/hexane gradient (20 to 25% EtOAc)

出典と根拠

ORDレコード
ord-b3944c55678647e2ba4a894eac9ab197
出典データセット
uspto-grants-2015_11
特許番号
US09187462B2

反応ノート

読み込み中…