Methanol → HCID 178443526, compound

HRID 1376373Notes

Reaction equation

HRID 1376373 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-9f3bb0bdc52e4e6b897970dab476235d
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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