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

HRID 495300

반응식

HRID 495300 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8058Hexane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-92705236b5794a5bb01450d143a7c481
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538241B2

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