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

HRID 9656

反応式

HRID 9656 の反応式
[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]

参加物

6

反応物 3

HCID 15096Tributyltin ChlorideHCID 129265222-(3-Methylthiophen-2-yl)-1,3-dioxolane2 回HCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bdd6a74b4fde4fe1a64ca556ea6560a2
出典データセット
uspto-grants-2006_08
特許番号
US07091237B2

関連ノート

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