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

HRID 6245

反応式

HRID 6245 の反応式
[CH2:1]([O:8][CH2:9][CH:10]([OH:20])[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]=O.[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26]>ClCCl.C(OCC)(=O)C>[CH2:13]([O:12][CH2:11][CH:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[O:20][CH2:21][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 712FormaldehydeHCID 31215Triethyl phosphiteHCID 2476141,3-Bis(benzyloxy)propan-2-ol

生成物 1

HCID 23055900Diethyl [2-benzyloxy-1-(benzyloxymethyl)ethoxy]methylphoshonate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  1. customDry HCl gas was bubbled through an ice-
  2. dry with materialThe resulting solution was dried (MgSO4)
  3. customevaporated to dryness
  4. customto leave an oil
  5. customThe liquid obtained
  6. washwashed with sodium bicarbonate solution
  7. washThe organic phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a mobile oil, which

出典と根拠

ORDレコード
ord-1159650d17344e7fa82a836be2dcb965
出典データセット
uspto-grants-1993_09
特許番号
US05247085

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