Methanol → HCID 178443526, compound

HRID 265401

Reaction equation

HRID 265401 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=[C:8]2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:33][P:34]([O:38]CC)[O:35][CH2:36][CH3:37].CO.O>C1(C)C=CC=CC=1>[CH2:36]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:8]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]=1)[CH3:37].[CH3:33][PH:34](=[O:35])[O-:38]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 85063Diethyl methylphosphoniteHCID 229164121,4,5-Triphenyl-2-(7-bromoheptyloxy)imidazole

Product 1

HCID 178443526HCID 178443526, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,4,5-triphenyl-2-(7-bromoheptyloxy)-imidazole (1.75 g) and diethyl methylphosphonite (2.45 g) in toluene (10 ml) was heated at reflux temperature for 48 hours. Methanol and water were added and the mixture evaporated to an oil. This was chromatographed on silica gel (ethyl acetate/ethanol). The resulting oil slowly crystallised and was triturated with ether/petroleum ether, filtered then recrystallised from ethanol/ether to give ethyl 7-(1,4,5-triphenyl-imidazol-2-yloxy)heptane-methylphosphinate (1.06 g, 57%) as a white solid, m.p. 101°-2° C. Found: C, 72.05; H, 7.26; N, 5.52%; C31H37N2O3P; Requires: C, 72.07; H, 7.22; N, 5.42%.

Workup

  1. temperatureat reflux temperature for 48 hours
  2. customthe mixture evaporated to an oil
  3. customThis was chromatographed on silica gel (ethyl acetate/ethanol)
  4. customThe resulting oil slowly crystallised
  5. customwas triturated with ether/petroleum ether
  6. filtrationfiltered
  7. customthen recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-b4e6be7428ea45bfb31e2b127adfab45
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Linked notes

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