Tert-Butanesulfinamide → HCID 88924920, 화합물

HRID 2279438노트

반응식

HRID 2279438 반응식
[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]

참가 물질

5

반응물 2

HCID 3382465Tert-ButanesulfinamideHCID 118293725-OXAZOLECARBOXALDEHYDE

생성물 1

HCID 88924920HCID 88924920, 화합물수율 58.7%

시약·촉매·용매 2

HCID 178477244HCID 178477244, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

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 placed in THF (15 mL) and heated to 65° C. for 12 h. 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 concentrated. The resulting residue was purified by SiO2 chromatography (20-25% EtOAc/hexane) to afford (E)-2-methyl-N-(oxazol-5-ylmethylene)propane-2-sulfinamide (20, 1.211 g, 6.047 mmol, 58.70% yield).

후처리

  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. concentrationthe organic layer was concentrated
  7. customThe resulting residue was purified by SiO2 chromatography (20-25% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-05e6ef8847164722b766abf4113903ff
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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