Triethyl phosphite → 3-[3-(Octadecyloxy)-5-(phenylmethoxycarbonyl)phenoxy]propylphosphonic acid diethyl ester

HRID 1757828Notes

Reaction equation

HRID 1757828 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:40])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([O:35][CH2:36][CH2:37][CH2:38]Br)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[P:41]([O:48]CC)([O:45][CH2:46][CH3:47])[O:42][CH2:43][CH3:44]>>[CH2:43]([O:42][P:41]([CH2:38][CH2:37][CH2:36][O:35][C:12]1[CH:11]=[C:10]([C:9]([O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:40])[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=1)(=[O:48])[O:45][CH2:46][CH3:47])[CH3:44]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 539190843-(3-Bromopropoxy)-5-(octadecyloxy)benzoic acid phenylmethyl ester

Product 1

HCID 541469353-[3-(Octadecyloxy)-5-(phenylmethoxycarbonyl)phenoxy]propylphosphonic acid diethyl esterYield 60%

Procedure

A mixture of 4.91 g (7.95 mmol) of 3-(3-bromopropoxy)-5-(octadecyloxy)benzoic acid phenylmethyl ester and 1.5ml (8.74 mmol) of triethyl phosphite was stirred and heated at 150° for 32 horns. Purification by chromatography on 250 g of silica gel gave 3.2 g (60% yield) of 3-[3-(octadecyloxy)-5-(phenylmethoxycarbonyl)phenoxy]propylphosphonic aciddiethyl ester as an oil. The structure was confirmed by the nmr spectrum.

Workup

  1. temperatureheated at 150° for 32 horns
  2. customPurification by chromatography on 250 g of silica gel

Sources & evidence

ORD record
ord-fea54ba040eb448fa341c775633d372c
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

Loading…