Ammonium Chloride → HCID 69733599, compound

HRID 1058155Notes

Reaction equation

HRID 1058155 reaction equation
Br[CH2:2][CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2.[CH2:10]([O:12][CH:13](OCC)[CH:14]=[CH2:15])[CH3:11].[Cl-].[NH4+]>O1CCCC1.[Cu]Br>[CH2:10]([O:12][CH:13]=[CH:14][CH2:15][CH2:2][CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2)[CH3:11]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 624773,3-Diethoxy-1-propeneHCID 27760625-(bromomethyl)bicyclo[2.2.1]hept-2-ene

Product 1

HCID 69733599HCID 69733599, compound

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent was customarily prepared from 200 g of 5-bromomethyl-2-norbornene in 500 ml of dry tetrahydrofuran. The Grignard reagent was added dropwise over one hour to a mixture of 130 g of 3,3-diethoxy-1-propene, 1.0 g of copper (I) bromide and 300 ml of dry tetrahydrofuran at 20° C. Stirring was continued for 20 hours whereupon the reaction solution was added to a saturated aqueous solution of ammonium chloride to stop reaction. After hexane extraction, the organic layer was successively washed with water, saturated sodium bicarbonate water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum, yielding 5-(4-ethoxy-3-buten-1-yl)-2-norbornene.

Workup

  1. customreaction
  2. extractionAfter hexane extraction
  3. washthe organic layer was successively washed with water, saturated sodium bicarbonate water and saturated sodium chloride water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-50c01b4ea6974fe38f8b9f8c8573affd
Source dataset
uspto-grants-2003_02
Patent number
US06515149B2

Reaction notes

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