Tert-Butanesulfinamide → HCID 88924920, 화합물

HRID 715057노트

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HRID 715057 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 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).

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. 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)

출처 및 근거

ORD 기록
ord-b3944c55678647e2ba4a894eac9ab197
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187462B2

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