Hexamethylditin → Trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane

HRID 1582891노트

반응식

HRID 1582891 반응식
C[Sn](C)C.C[Sn](C)C.[CH3:9][Sn:10]([CH3:25])([CH3:24])[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([O:20]C)=[C:13]([O:22][CH3:23])[CH:12]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][Sn:10]([CH3:25])([CH3:24])[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]2[O:20][CH2:23][O:22][C:13]=2[CH:12]=1

참가 물질

5

반응물 2

HCID 6327618HexamethylditinHCID 10759980Trimethyl(3,4-dimethoxy-6-nitrophenyl)stannane

생성물 1

HCID 10782610Trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane수율 54%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of hexamethylditin (1 g, 3.1 mmol), compound 16 (0.7 g, 2.9 mmol) and tetrakis(triphenylphosphine)palladium (100 mg) in anhydrous THF (20 ml) was heated to reflux under nitrogen for 10 h. After cooling to room temperature, THF was evaporated and methylene chloride (30 mL) was added to the residue. To this mixture, aqueous potassium fluoride (7.0M, 1 mL) was added dropwise with vigorous stirring. The mixture was passed through a Celite bed and the filtrate was washed with brine. The methylene chloride layer was dried (anhydrous Na2SO4), filtered and evaporated in vacuo. The residue was chromatographed using 95:5 hexanes:ethyl acetate to give 62 (0.5 g) in 54% yield; 1H NMR (CDCl3) δ0.32 (9H, s), 6.12 (2H, s), 7.04 (1H, s), 7.82 (1H, s); 13C NMR (CDCl3) δ−6.94, 103.27, 105.82, 114.76, 137.19, 147.90, 149.36, 153.36; HRMS (EI) calcd for C10H13NO4Sn—CH3 m/z: 315.9632; found: 315.9638.

후처리

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 10 h
  3. customTHF was evaporated
  4. additionmethylene chloride (30 mL) was added to the residue
  5. additionTo this mixture, aqueous potassium fluoride (7.0M, 1 mL) was added dropwise with vigorous stirring
  6. washthe filtrate was washed with brine
  7. dry with materialThe methylene chloride layer was dried (anhydrous Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was chromatographed

출처 및 근거

ORD 기록
ord-2d37d606643642b3a5ceac9555e08e7d
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740650B2

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