Hydrochloric Acid → HCID 20131142, compound

HRID 1380133Notes

Reaction equation

HRID 1380133 reaction equation
[OH:1][C:2](C)([CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[CH3:21]C(C)([O-])C.[K+].Br[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].Cl>CS(C)=O.O>[N:4]1([CH:3]([CH3:21])[CH:2]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[O:1][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 117544Ethyl 6-bromohexanoateHCID 20131141HCID 20131141, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20131142HCID 20131142, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 1-[2-hydroxy-2-methyl-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (3.2 g, 0.0116 mol) in dimethylsulphoxide (20 ml) at 10° C., potassium tert butoxide (2.1 g, 0.018 mol) was added in portions over 10 min. CAUTION (see, L. Bretherick, Royal Society of Chemistry, Hazards in the Chemical Laboratory, 3rd Ed. p. 307). After stirring for 5 mins. a solution of ethyl 6-bromohexanoate (2.58 g, 0.0116 mol) in dimethyl sulphoxide (5 ml) was added, the reaction mixture warmed to room temperature, and stirring continued for a further 45 min. The mixture was poured into water, neutralised with 1N hydrochloric acid and extracted with dichloromethane. The combined organic extracts were washed with water, dried (MgSO4) and solvent removed at reduced pressure. The title compound was isolated by column chromatography (silica gel, 3% ethanol in chloroform) as a yellow oil.

Workup

  1. stirringstirring
  2. waitcontinued for a further 45 min
  3. extractionextracted with dichloromethane
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (MgSO4) and solvent
  6. customremoved at reduced pressure

Sources & evidence

ORD record
ord-c720f397ff0a4f47a9223e8573274918
Source dataset
uspto-grants-1986_04
Patent number
US04579862

Reaction notes

Loading…