Diethyl Ether → HCID 54574644, compound

HRID 1414837Notes

Reaction equation

HRID 1414837 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH:6]12[CH2:12][CH:9]([CH:10]=[CH:11]1)[CH:8]=[CH:7]2.C([O:15]CC)C>>[CH:2]12[CH2:1][CH:9]([CH:10]=[CH:11]1)[CH:8]1[CH:3]2[CH:6]([CH2:12][OH:15])[CH2:7]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 8473NorbornadieneHCID 178455850HCID 178455850, compound

Product 1

HCID 54574644HCID 54574644, compoundYield 73%

Procedure

The procedure of Example I was repeated on a larger scale by reacting 195 mmoles of allylmagnesium bromide in diethyl ether with 218 mmoles of bicyclo[2.2.1]hepta-2,5-diene at 125° C. for 3 hours. After the oxidation and hydrolysis, distillation gave tricyclo[4.2.1.02.5 ]non-7-en-3-yl-methanol (b.p. 97°-99° C. at 1 mm Hg) in 73 percent yield based on the allylmagnesium bromide.

Workup

  1. customat 125° C.
  2. customfor 3 hours
  3. customAfter the oxidation and hydrolysis, distillation

Sources & evidence

ORD record
ord-ee87587f7e3e405e8575e72d6ae99334
Source dataset
uspto-grants-1977_01
Patent number
US04002691

Reaction notes

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