Hydrogen Peroxide → 6-Carbomethoxymethyl-6-ethyl-2-cyclohexen-1-one

HRID 256222

반응식

HRID 256222 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1([CH2:12][CH3:13])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11].C1([Se]Cl)C=CC=CC=1.O.OO>C(OCC)(=O)C.O1CCCC1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1([CH2:12][CH3:13])[CH2:10][CH2:9][CH:8]=[CH:7][C:6]1=[O:11]

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 21928ChloroselenobenzeneHCID 122920281-Ethyl-2-oxocyclohexaneacetic Acid Methyl Ester

생성물 1

HCID 136492416-Carbomethoxymethyl-6-ethyl-2-cyclohexen-1-one수율 55.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

The ketone, 2-carbomethoxymethyl-2-ethylcyclohexanone (IX) (141 mmol, 28 g) was stirred in 1.25 l of ethyl acetate (dried over 3A molecular sieves) and treated with 169 mmol (32.5 g) of PhSeCl. The reaction was stirred under nitrogen for 4 hours then treated with 250 mL of water. The mixture was shaken vigorously in a separatory funnel and the organic phase was returned to the reaction flask. Tetrahydrofuran (550 mL) was then added followed by 35 mL of 30% H2O2 (aq.) added dropwise. The reaction mixture was stirred for one hour then washed with 500 mL of water and 500 mL of saturated Na2CO3 (aq.). The product was then dried over MgSO4 and concentrated in vacuo. Flash chromatography (4 inches diameter column, 20% ethyl acetate in petroleum ether eluent, 51/2 inches of silica gel) afforded 15.3 g (78.0 mmol, 55%) of the product as a pale yellow oil. Rf =0.9 in 15% ethyl acetate/petroleum ether on TLC.

후처리

  1. stirringThe mixture was shaken vigorously in a separatory funnel
  2. additionadded dropwise
  3. stirringThe reaction mixture was stirred for one hour
  4. washthen washed with 500 mL of water and 500 mL of saturated Na2CO3 (aq.)
  5. dry with materialThe product was then dried over MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-09a5377079f34b5099f2a44d4daee215
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04701533

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