Acetone → Diethyl 3,4-dihydroxybutylphosphonate

HRID 373885노트

반응식

HRID 373885 반응식
[CH2:1]([P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])[CH2:2]C=C.C[N+]1([O-])[CH2:19][CH2:18][O:17]CC1.CC(C)=[O:23]>O.[Os](=O)(=O)(=O)=O>[OH:23][CH:19]([CH2:18][OH:17])[CH2:2][CH2:1][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8]

참가 물질

6

반응물 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 10997850Diethyl 3-butenylphosphonate

생성물 1

HCID 19808663Diethyl 3,4-dihydroxybutylphosphonate수율 71%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 962Water용매

실험 절차

To a solution of diethyl but-3-enylphosphonate (10.2 g, 0.053 mol) in acetone (200 ml) and water (40 ml), was added a trace of osmium tetroxide (1 mg). After stirring for 10 minutes at ambient temperature, 4-methylmorpholine-N-oxide (10.75 g, 0.079 mol) was added in one portion. Stirring was continued overnight under an atmosphere of nitrogen. The solution was concentrated under reduced pressure, and final traces of water removed by azeotroping with benzene and ethanol. The residual brown oil was chromatographed on silica gel (dichloromethane-methanol, 95:5 as eluant) to give the title compound as an oil (8.5 g, 71%). IR: υmax (film), 3400, 3000, 2940, 2880, 1450, 1400, 1230, 1170, 1070, 1030, 970, 820, 790 cm-1. 1H NMR: δH ((CD3)2SO) 1.25 (6H, t, J=8Hz, (OCH2CH3)2), 1.3-2.05 (4H, m, CH2CH2P), 3.1-3.5 (3H, m, HOCH2CH(OH)), 4.0 (4H, m, (OCH2CH3)2), 4.6 (2H, m, D2O exchangeable, HOCH2CH(OH)). Found: C, 42.57; H, 8.56%. C8H19O5P requires: C, 42.47; H, 8.46%. m/z:C8H20O5P requires 227.1048; observed: 227.1045 (MH+).

후처리

  1. stirringStirring
  2. waitwas continued overnight under an atmosphere of nitrogen
  3. concentrationThe solution was concentrated under reduced pressure
  4. customfinal traces of water removed
  5. customby azeotroping with benzene and ethanol
  6. customThe residual brown oil was chromatographed on silica gel (dichloromethane-methanol, 95:5 as eluant)

출처 및 근거

ORD 기록
ord-a6cc4d4ed7a04d11adaf2dfa16fe62e4
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166198

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