Tributyltin Chloride → Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane

HRID 366859

反応式

HRID 366859 の反応式
C([Li])CCC.[CH2:6]1[CH2:14][O:13][C:12]2[C:8](=[CH:9][S:10][CH:11]=2)[O:7]1.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>C1COCC1>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:9]1[S:10][CH:11]=[C:12]2[O:13][CH2:14][CH2:6][O:7][C:8]=12)[CH2:25][CH2:26][CH3:27]

参加物

5

反応物 3

HCID 15096Tributyltin ChlorideHCID 44218643,4-EthylenedioxythiopheneHCID 178418339Butyllithium

生成物 1

HCID 15891053Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

n-Butyllithium (77 mL, 192.5 mmol, 2.5 M solution in hexane) was added dropwise at -78° C. to a solution of 3,4-(ethylenedioxy)thiophene (25 g, 175.9 mmol) in anhydrous THF (100 mL) under nitrogen. The solution was stirred for 1 h and warmed to -40° C. Tributylstannyl chloride (85.89 g, 263.9 mmol) was added and the entire solution was finally allowed to warm to room temperature. At room temperature the mixture was filtered using Celite and the solvent was stripped. The organo-tin compound was vacuum dried to give 2-(tributylstannyl)-3,4-(ethylenedioxy)thiophene, obtained as a dark yellow liquid, yield=98%. MS(EI) m/z (rel int): 375 [(M)+ --C4H8, 100%] and 319[(M)+ --C8H16, 18%].

後処理

  1. temperatureto warm to room temperature
  2. filtrationAt room temperature the mixture was filtered
  3. customdried

出典と根拠

ORDレコード
ord-891cc2ba15b04d7b843f32e705f27aa2
出典データセット
uspto-grants-2000_10
特許番号
US06130339

関連ノート

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