1,1-Dibromoethane → 2-Hydroxy-2-adamantylethyl Vinyl Ether

HRID 22623

Reaction equation

HRID 22623 reaction equation
[Mg].BrC(Br)C.[CH:6]([O:8][CH2:9][CH2:10]CCl)=[CH2:7].[CH:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[C:14]1=[O:23])[CH2:20]2>O.OS(O)(=O)=O.C1COCC1>[CH:6]([O:8][CH2:9][CH2:10][C:14]1([OH:23])[CH:15]2[CH2:21][CH:19]3[CH2:18][CH:17]([CH2:22][CH:13]1[CH2:20]3)[CH2:16]2)=[CH2:7]

Participants

8

Reactant 4

HCID 112011,1-DibromoethaneHCID 64151AdamantanoneHCID 5462224MagnesiumHCID 221862153-Chloropropyl vinyl ether

Product 1

HCID 865900622-Hydroxy-2-adamantylethyl Vinyl Ether

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

(Step-2) Magnesium metal(2.6 g) and anhydrous tetrahydrofuran (hereinafter referred to as THF(100 mL)) were added to a round bottom flask. Next, after dripping a small quantity of dibromoethane into the round bottom flask containing the resulting mixture to promote the reaction, 3-chloropropyl vinyl ether (12 g, 0.1 mol) and anhydrous THF(100 mL) were added drop-wise thereto. Then, the mixture was reacted for 2 hours. After dripping an adequate quantity of THF containing 2-adamantanone (15 g, 0.1 mol) in the mixture, the resulting mixture was refluxed for 12 hours. After the reaction was completed, the reaction mixture was slowly dissolved in excessive water and neutralized with thin H2SO4 solution. Then, the organic layer was extracted from the reaction solution using an adequate quantity of diethyl ether and then dried with anhydrous sodium sulfate. Next, after evaporating the solvent to obtain an oily residue using a rotary evaporator, the product was separated using a column chromatography method (hexane:ethyl acetate=3:1). (Yield: 60%)

Workup

  1. additionwere added to a round bottom flask
  2. additioncontaining the resulting mixture
  3. additionwere added drop-wise
  4. customThen, the mixture was reacted for 2 hours
  5. temperaturethe resulting mixture was refluxed for 12 hours
  6. extractionThen, the organic layer was extracted from the reaction solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. customNext, after evaporating the solvent
  9. customto obtain an oily residue
  10. customa rotary evaporator
  11. customthe product was separated

Sources & evidence

ORD record
ord-8ba09fd2cc7646759768ea7fc99b2cf3
Source dataset
uspto-grants-2005_02
Patent number
US06849378B2

Linked notes

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