Sodium ethoxide → Diethyl 2-hydroxyethoxymethanephosphonate

HRID 6242

반응식

HRID 6242 반응식
C([O:4][CH2:5][CH2:6][O:7][CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])(=O)C.[O-]CC.[Na+]>C(O)C>[OH:4][CH2:5][CH2:6][O:7][CH2:8][P:9](=[O:16])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15]

참가 물질

4

반응물 2

HCID 2723922Sodium ethoxideHCID 139159842-((Diethoxyphosphoryl)methoxy)ethyl acetate

생성물 1

HCID 10262588Diethyl 2-hydroxyethoxymethanephosphonate수율 70%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of diethyl 2-acetoxyethoxymethylphosphonate* (16 g, 63 mmol) in absolute ethanol (150 ml), was added 0.5M sodium ethoxide (12.19 ml). After standing at ambient temperature overnight, 1R-120H resin was added until pH 6.5 was reached. The solution was filtered immediately, the resin washed with ethanol and the combined filtrates evaporated under reduced pressure. The residue was chromatographed on silica gel (eluted with chloroform: methanol, 98:2) to yield the title compound as a colourless oil (9.3g, 70%). IR: νmax (film) 3420, 3000, 1450, 1395, 1240, 1170, 1130, 1030, 970 cm-1. 1H NMR: δH (CDCl3) 1.35 (6H,t,J=7Hz, (OCH2CH3)2), 3.75 (4H,br.s, OCH2CH2O), 3.90 (2H,d,J=8Hz, O--CH2P), 4.20 (4H,m,(O--CH2CH3)2), 5.20 (1H,br.s, D 2 O exchangeable, OH). Found: C,38.64; H,8.27%. C7H17PO5.0.3H2O requires: C,38.63; H,8.01%.

후처리

  1. filtrationThe solution was filtered immediately
  2. washthe resin washed with ethanol
  3. customthe combined filtrates evaporated under reduced pressure
  4. customThe residue was chromatographed on silica gel (eluted with chloroform: methanol, 98:2)

출처 및 근거

ORD 기록
ord-86fb1dcff3c742f79157360a3f708f8a
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05247085

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