Sodium ethoxide → Diethyl 2-hydroxyethoxymethanephosphonate

HRID 6242

反応式

HRID 6242 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 10262588Diethyl 2-hydroxyethoxymethanephosphonate収率 70%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-86fb1dcff3c742f79157360a3f708f8a
出典データセット
uspto-grants-1993_09
特許番号
US05247085

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