Tributyltin Chloride → Tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane

HRID 9656

반응식

HRID 9656 반응식
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[O:11][CH2:10][CH2:9][O:8]1.C([Li])CCC.[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>O1CCCC1.C(OCC)C>[CH2:26]([Sn:21]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:22][CH2:23][CH2:24][CH3:25])[C:5]1[S:4][C:3]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)=[C:2]([CH3:1])[CH:6]=1)[CH2:27][CH2:28][CH3:29]

참가 물질

6

반응물 3

HCID 15096Tributyltin ChlorideHCID 129265222-(3-Methylthiophen-2-yl)-1,3-dioxolane2회HCID 178418339Butyllithium

생성물 1

HCID 21986287Tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-60 °C

실험 절차

A mixture of 2-(3-methylthien-2-yl)-1,3-dioxolane (intermediate 75, 1.5 g) in tetrahydrofuran (50 ml), stirred at −60° C. under a nitrogen atmosphere, was treated drop-wise with 1.6M n-butyl lithium in hexanes (6.1 ml). The reaction mixture was stirred at this temperature for 1 hour and tributyltin chloride (2.6 ml) was added; stirring was continued at −60° C. for 1 hour and then the reaction allowed to warm to ambient temperature. After 18 hours the reaction mixture was diluted with diethylether and this mixture was extracted with water and the ether layer dried with brine and over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using cyclohexane:ethyl acetate (50:1) as eluent to give the title compound as a yellow oil.

후처리

  1. stirringThe reaction mixture was stirred at this temperature for 1 hour
  2. stirringstirring
  3. temperatureto warm to ambient temperature
  4. extractionthis mixture was extracted with water
  5. dry with materialthe ether layer dried with brine and over magnesium sulfate
  6. customThe product isolated
  7. customafter evaporation of the solvent
  8. customwas further purified by flash column chromatography

출처 및 근거

ORD 기록
ord-bdd6a74b4fde4fe1a64ca556ea6560a2
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091237B2

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