Propylene Oxide → 2-(1h-imidazol-1-yl)propan-1-ol

HRID 1591072Notes

Reaction equation

HRID 1591072 reaction equation
Cl.[N:2]1([CH2:7][CH:8]([CH3:14])[O:9][CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:5][N:4]=[CH:3]1.[Na].O[C:17](P(O)(=O)O)(P(O)(=O)O)COC(C)CN1C=CN=C1.[CH2:36]1O[CH:37]1C>>[N:2]1([CH:7]([CH3:17])[CH2:8][OH:9])[CH:6]=[CH:5][N:4]=[CH:3]1.[CH2:36]([O:12][C:11](=[O:13])[CH2:10][O:9][CH:8]([CH3:14])[CH2:7][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1)[CH3:37]

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 5360545SodiumHCID 197663375-(Imidazol-1-yl)-4-methyl-3-oxa-pentanoic acid-hydrochlorideHCID 197663941-Hydroxy-5-(imidazol-1-yl)-4-methyl-3-oxa-pentane-1,1-diphosphonic acid

Product 2

HCID 1091472-(1h-imidazol-1-yl)propan-1-olHCID 179907055-(Imidazol-1-yl)-4-methyl-3-oxa-pentanoic acid-ethyl ester

Procedure

The 5-(imidazol-1-yl)-4-methyl-3-oxa-pentanoic acid-hydrochloride used as the starting material was prepared in the following manner: reaction of the sodium salt of the imidazole with propene oxide yields the 2-(imidazol-1-yl)-1-propanol (b.p.0.1 : 147°-150° C.) from which the 5-(imidazol-1-yl)-4-methyl-3-oxa-pentanoic acid-ethyl ester (oil) is obtained by reaction with ethyl bromoacetate in dimethyl formamide in the presence of sodium hydride which is then saponified with 3N hydrochloric acid to form the desired acid.

Workup

  1. customwas prepared in the following manner

Sources & evidence

ORD record
ord-b5100ed72aef45b9b741de2fb1877cdf
Source dataset
uspto-grants-1993_04
Patent number
US05206253

Reaction notes

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