Chlorotrimethylsilane → 2-acetyltrop-2-ene

HRID 1464593ノート

反応式

HRID 1464593 の反応式
[C@@H:1]12[N:8]([CH3:9])[C@@H:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]=[C:2]2[C:10]([O:12]CC)=O.[Si](Cl)(C)(C)[CH3:16].[Li]C>C1COCC1>[C:10]([C:2]1[C@@H:1]2[N:8]([CH3:9])[C@H:5]([CH2:4][CH:3]=1)[CH2:6][CH2:7]2)(=[O:12])[CH3:16]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 25222744Ecgonidine ethyl esterHCID 178418348HCID 178418348、化合物

生成物 1

HCID 108774782-acetyltrop-2-ene収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-100 °C

実験手順

To a mixture of ethyl trop 2-ene-2-carboxylate (3.43 g, 0.019 mol) and Me3SiCl (10.32 g, 0.095 mol) in THF (70 mL) cooled to -100° C., MeLi (1.4M, 17.07 mL, 0.0239 mol) was added dropwise. After warming up to room temperature, the reaction mixture was stirred for 16 hours. Excess Me3SiCl and THF was evaporated off and the resulting residue was stirred with EtOH (6 mL) followed by water (6 mL). The mixture was then made acidic (6N HCl) and extracted with ether. The aqueous layer was made basic (solid K2CO3) and extracted with chloroform, dried (K2CO3) and concentrated to give 3.14 g (81%) of 2-acetyltrop-2-ene as an oil: IR (neat) 1670 (COCH3); 1H NMR (CDCl3) δ6.7 (bt, 1H), 2.3 (s, NCH3), 2.2 (s, C(≡O)CH3).

後処理

  1. temperatureAfter warming up to room temperature
  2. customExcess Me3SiCl and THF was evaporated off
  3. stirringthe resulting residue was stirred with EtOH (6 mL)
  4. extractionmade acidic (6N HCl) and extracted with ether
  5. extractionextracted with chloroform
  6. dry with materialdried (K2CO3)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2f175e7851544622b48024d1d9cce427
出典データセット
uspto-grants-1994_04
特許番号
US05306718

反応ノート

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