반응 #6341

반응 방정식

1,3-dibenzyloxypropan-2-ol

paraformaldehyde

Triethyl phosphite

→

title compound

Diethyl [2-benzyloxy-1-(benzyloxymethyl)ethoxy]methylphoshonate

용매

dichloromethane

ethyl acetate

반응 조건

후처리

1. 1
   기타Dry HCl gas was bubbled through an ice-
2. 2
   건조The resulting solution was dried (MgSO4)
3. 3
   기타evaporated to dryness
4. 4
   기타to leave an oil
5. 5
   기타The liquid obtained
6. 6
   세척washed with sodium bicarbonate solution
7. 7
   세척The organic phase was washed with brine
8. 8
   건조dried (MgSO4)
9. 9
   기타evaporated
10. 10
    기타to give a mobile oil, which

실험 절차

Dry HCl gas was bubbled through an ice-cooled solution of 1,3-dibenzyloxypropan-2-ol (25 g, 0.092 mol) and paraformaldehyde (2.75 g, 0.092 mol) in dry dichloromethane (100 ml) for 1 hour. The resulting solution was dried (MgSO4) and evaporated to dryness to leave an oil. Triethyl phosphite (15.7 ml, 0.092 mol) was added and the resulting mixture stirred and heated at 140° C. for 16 hours. The liquid obtained was dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was washed with brine, dried (MgSO4) and evaporated to give a mobile oil, which was chromotographed in silica (hexane/ethyl acetate 50:50 as eluant) to give the title compound as a colourless, mobile oil (19.7 g, 51). IR: νmax (film) 3055, 3020, 2900, 2860, 1490, 1470, 1450, 1390, 1305, 1255, 1095, 1050, 1030, 970, 820, 770, 735, 700 cm-1. 1H NMR: δH (CDCl3) 1.3 (6H, t, J=7 Hz, P-(OCH2CH3)2), 3.6 (4H, d, 2×CH2OCH2Ph),3.8-4.05 (1H, m, CH), 4.05 (2H, d, J=9 Hz, OCH2P), 4.0-4.3 (4H, m, P-(OCH2CH3)2), 4.55 (4H, s, 2×OCH2Ph), 7.38 (10H, s, 2×Ph). C22H31PO6 requires: C, 62.54; H, 7.42. Found: C, 62.75, H, 7.61. m/z: C22H31PO6 requires 422.1858; observed (M+) 422.1864.

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