Tetrahydrofuran → Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]-

HRID 495300

反応式

HRID 495300 の反応式
O1CCCC1.[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[O:12][CH:13]=[CH:14][CH:15]=1.C([Li])CCC.[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24]>O.CCCCCC>[CH2:30]([Sn:25]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:26][CH2:27][CH2:28][CH3:29])[C:13]1[O:12][C:11]([CH:7]2[O:8][CH2:9][CH2:10][O:6]2)=[CH:15][CH:14]=1)[CH2:31][CH2:32][CH3:33]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 15096Tributyltin ChlorideHCID 2631582-Furyl-1,3-dioxolaneHCID 178418339Butyllithium

生成物 1

HCID 10960952Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]-収率 75.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8058Hexane溶媒

実験手順

Tetrahydrofuran (10 mL) solution of 2-(1,3-dioxolan-2-yl)furan (1.0 g, 7.1 mmol) was cooled to −78° C., and n-hexane solution of 1.6 mol/L n-butyllithium (4.5 mL, 7.2 mmol) was dropwise added thereto, and stirred for 3 hours. Tributyltin chloride (2.6 g, 7.9 mmol) was dropwise added to the reaction mixture, and stirred for 5 hours with heating up to room temperature. Water (10 mL) was added to the reaction mixture, and extracted with ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (n-hexane to ethyl acetate/n-hexane=1/20) to obtain tributyl[5-(1,3-dioxolan-2-yl)furan-2-yl]tin (2.3 g, 75%).

後処理

  1. stirringstirred for 5 hours
  2. extractionextracted with ethyl acetate (50 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (n-hexane to ethyl acetate/n-hexane=1/20)

出典と根拠

ORDレコード
ord-92705236b5794a5bb01450d143a7c481
出典データセット
uspto-grants-2009_05
特許番号
US07538241B2

関連ノート

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