Hydrochloric Acid → 2,3,8a-trimethyl-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone

HRID 645333

반응식

HRID 645333 반응식
[CH2:1]([Al](Cl)Cl)[CH3:2].[CH3:6][C:7]1[C:8](=[O:15])[CH:9]([CH3:14])[CH:10]([CH3:13])[CH2:11][CH:12]=1.[CH2:16]=[CH:17]C=C.Cl>C(Cl)Cl>[CH3:14][CH:9]1[CH:10]([CH3:13])[CH2:11][CH:12]2[C:1]([CH3:2])([CH2:16][CH:17]=[CH:6][CH2:7]2)[C:8]1=[O:15]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 78451,3-ButadieneHCID 11237Ethylaluminum dichlorideHCID 892642-Cyclohexen-1-one, 2,5,6-trimethyl-

생성물 1

HCID 574294412,3,8a-trimethyl-3,4,4a,5,8,8a-hexahydro-1(2H)-naphthalenone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 1 liter round-bottomed flask, at room temperature, were successively added CH2Cl2 (400 ml), BHT (100 mg) and a 1 M solution of EtAlCl2 in hexanes (80 ml; 0.08 mol). 2,5,6-trimethylcyclohex-2-en-1-one (55.2 g, 0.4 mol, 3:2 mixture of two isomers) was added dropwise, while maintaining the internal temperature below 30° C. Then butadiene (43.2 g, 0.8 mol) was added in one portion. The reaction was stirred at room temperature for 15 days. The reaction was then poured onto cold 5% aqueous HCl and extracted twice with ether. The organic layers were washed with saturated aqueous NaHCO3, water and brine and dried over solid sodium sulfate. The crude product was distilled to give 50 g of a liquid which was then chromatographed on silicagel (heptane:ethyl acetate 49:1) then purified by bulb-to-bulb distillation (B.P.=90° C./0.021 mbar) to give the totle compound (39.43 g, 0.205 mol, 51%) as a 3:2 mixture of diastereoisomers.

후처리

  1. customIn a 1 liter round-bottomed flask, at room temperature, were successively added
  2. temperaturewhile maintaining the internal temperature below 30° C
  3. extractionextracted twice with ether
  4. washThe organic layers were washed with saturated aqueous NaHCO3, water and brine
  5. dry with materialdried over solid sodium sulfate
  6. distillationThe crude product was distilled

출처 및 근거

ORD 기록
ord-579305bd9e9742e297fe5c0214d13473
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704933B2

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