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

HRID 645333

反応式

HRID 645333 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-579305bd9e9742e297fe5c0214d13473
出典データセット
uspto-grants-2010_04
特許番号
US07704933B2

関連ノート

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