Ethyl Bromide → HCID 20068382, compound

HRID 1638257Notes

Reaction equation

HRID 1638257 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-01ca9307d0744229a0350b0d14093a60
Source dataset
uspto-grants-1989_11
Patent number
US04878940

Reaction notes

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