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

HRID 1582891ノート

反応式

HRID 1582891 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2d37d606643642b3a5ceac9555e08e7d
出典データセット
uspto-grants-2004_05
特許番号
US06740650B2

反応ノート

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