Chlorotrimethylsilane → 2-acetyltrop-2-ene

HRID 1464593노트

반응식

HRID 1464593 반응식
[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]

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 25222744Ecgonidine ethyl esterHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 108774782-acetyltrop-2-ene수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2f175e7851544622b48024d1d9cce427
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306718

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