18-Crown-6 → 2-Nitro-2-methyl-1-[di-(t-butyl)methoxy]propane

HRID 746190

反応式

HRID 746190 の反応式
[C:1]([CH:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[OH:6])([CH3:4])([CH3:3])[CH3:2].[CH:11]([Li])(CC)C.C1OCCOCCOCCOCCOCCOC1.[N+:34]([C:37]([CH3:39])=[CH2:38])([O-:36])=[O:35]>C(#N)C.O1CCCC1>[N+:34]([C:37]([CH3:11])([CH3:39])[CH2:38][O:6][CH:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:1]([CH3:4])([CH3:3])[CH3:2])([O-:36])=[O:35]

参加物

7

反応物 4

HCID 2855718-Crown-6HCID 784862-Nitro-1-propeneHCID 1397902,2,4,4-Tetramethylpentan-3-olHCID 178418400CID 53628100

生成物 1

HCID 202012022-Nitro-2-methyl-1-[di-(t-butyl)methoxy]propane

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Di-t-butylmethanol is added to a dry flask under argon at 0° C. Dry tetrahydrofuran is added with a syringe. Sec-Butyl lithium (1.5M in Hexanes) is added quickly in one portion and the contents of the flask are stirred for one hour at room temperature. A 10 mM solution of 18-crown-6-ether in acetonitrile is added with a syringe and the flask cooled to 0° C. A tetrahydrofuran solution of 2-nitropropene is added with vigorous stirring over a 10 minute period. After completion of the reaction, as judged by thin layer chromatography, it is quenched with dimethyl sulfate, poured into saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield 2-nitro-2-methyl-1-[di-(t-butyl)methoxy]propane.

後処理

  1. temperaturethe flask cooled to 0° C
  2. stirringwith vigorous stirring over a 10 minute period
  3. customAfter completion of the reaction
  4. customis quenched with dimethyl sulfate
  5. additionpoured into saturated ammonium chloride
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer is dried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-86b608490e504dc195c6243a55d9afb4
出典データセット
uspto-grants-1986_07
特許番号
US04603011

関連ノート

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