Ethyl Bromide → HCID 20068382, compound

HRID 981874Notes

Reaction equation

HRID 981874 reaction equation
Br[CH2:2][CH3:3].[Mg].[CH:5]1([N:15]2[C:19]([CH:20]=[O:21])=[CH:18][N:17]=[CH:16]2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[OH-].[Na+]>O.O(CC)CC>[CH2:2]([CH:20]([C:19]1[N:15]([CH:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7][CH2:6]2)[CH:16]=[N:17][CH:18]=1)[OH:21])[CH3:3]

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 5462224MagnesiumHCID 20068372HCID 20068372, compound

Product 1

HCID 20068382HCID 20068382, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred and refluxed Grignard complex, previously prepared starting from 9 parts of bromoethane, 2.16 parts of magnesium and 140 parts of 1,1'-oxybisethane were added dropwise 11.3 parts of 1-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazole-5-carboxaldehyde. Upon complete addition, stirring was continued for 2 hours at room temperature. The reaction mixture was poured into water and treated with a sodium hydroxide solution. The separated organic layer was washed with water, dried, filtered and evaporated, yielding 4.6 parts (35.8%) of α-ethyl-1-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazole-5-methanol as a residue (compound 2.06).

Workup

  1. temperaturerefluxed Grignard complex
  2. custompreviously prepared
  3. additionUpon complete addition
  4. stirringstirring
  5. washThe separated organic layer was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6b6e493fc8fd4093bf65689374fde570
Source dataset
uspto-grants-1991_02
Patent number
US04994103

Reaction notes

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