Trimethyltin chloride → (5-Hexylthiophen-2-yl)trimethylstannane

HRID 384240ノート

反応式

HRID 384240 の反応式
[CH2:1]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Li]CCCC.[CH3:17][Sn:18](Cl)([CH3:20])[CH3:19]>C1COCC1>[CH2:1]([C:7]1[S:8][C:9]([Sn:18]([CH3:20])([CH3:19])[CH3:17])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 14016Trimethyltin chlorideHCID 877932-HexylthiopheneHCID 178418339Butyllithium

生成物 1

HCID 11267529(5-Hexylthiophen-2-yl)trimethylstannane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

2-Hexylthiophene (23.0 g, 0.137 mol) was dissolved in 250 ml THF and n-BuLi (94 ml, 1.6 M in hexanes, 0.150 mol) was added dropwise at 0° C. The mixture was stirred at 0° C. for 1 h and then cooled down to −78° C. A solution of trimethyltin chloride (32.8 g, 0.164 mol) in 100 ml THF was added dropwise. The mixture was allowed to warm slowly to room temperature and stirred for 2 h. After quenching with ice water and aqueous work-up, the product was distilled at 108° C. under high vacuum. 5-Hexyl-2-trimethylstannylthiophene was obtained as a colourless liquid (40.8 g, 90% yield).

後処理

  1. temperaturecooled down to −78° C
  2. temperatureto warm slowly to room temperature
  3. stirringstirred for 2 h
  4. customAfter quenching with ice water and aqueous work-up
  5. distillationthe product was distilled at 108° C. under high vacuum

出典と根拠

ORDレコード
ord-2378c8f1859d44b5abecde2703876fa2
出典データセット
uspto-grants-2013_02
特許番号
US08367717B2

反応ノート

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