Acetaldehyde → 2-(2-Ethyl-2-bicyclo[2.2.1]-heptyloxycarbonyl)propyl 2-norbornene-5-carboxylate

HRID 434197

Reaction equation

HRID 434197 reaction equation
[OH:1][CH:2](C)[CH2:3][C:4]([O:6][C:7]1([CH2:14][CH3:15])[CH2:12][CH:11]2[CH2:13][CH:8]1[CH2:9][CH2:10]2)=[O:5].[C:17](OC1(CC)CC2CC1CC2)(=O)C.C(=O)C.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH:43]12[CH2:52][CH:46]([CH:47]([C:49](Cl)=[O:50])[CH2:48]1)[CH:45]=[CH:44]2>C(Cl)Cl.CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH:43]12[CH2:52][CH:46]([CH:47]([C:49]([O:1][CH2:2][CH:3]([C:4]([O:6][C:7]3([CH2:14][CH3:15])[CH2:12][CH:11]4[CH2:13][CH:8]3[CH2:9][CH2:10]4)=[O:5])[CH3:17])=[O:50])[CH2:48]1)[CH:45]=[CH:44]2

Participants

9

Reactant 5

HCID 177AcetaldehydeHCID 98233Bicyclo(2.2.1)hept-5-ene-2-carbonyl chlorideHCID 5643932-Ethyl-2-norbornyl acetateHCID 2733832Lithium HexamethyldisilazideHCID 187573362-Ethyl-2-bicyclo[2.2.1]heptyl 3-hydroxybutanoate

Product 1

HCID 187573352-(2-Ethyl-2-bicyclo[2.2.1]-heptyloxycarbonyl)propyl 2-norbornene-5-carboxylateYield 84.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In 350 ml of methylene chloride was dissolved 74.4 g of 2-ethyl-2-bicyclo[2.2.1]heptyl 3-hydroxybutanoate (which was synthesized by reacting 2-ethyl-2-bicyclo[2.2.1]heptyl acetate with acetoaldehyde in the presence of lithium hexamethyldisilazide). Then 39.0 g of pyridine and a catalytic amount of 4-(N,N-dimethylamino)pyridine were added to the solution, which was stirred under ice cooling. To this reaction mixture below 10° C., 66.8 g of 2-norbornene-5-carboxylic chloride was added dropwise over one hour. After agitation was continued for 3 hours, the reaction solution was worked up in a conventional manner. The resulting oily substance was purified by silica gel column chromatography, obtaining 96.7 g of 2-(2-ethyl-2-bicyclo[2.2.1]-heptyloxycarbonyl)propyl 2-norbornene-5-carboxylate, designated Monomer 1. The yield was 84.9%.

Workup

  1. customwas synthesized
  2. customThe resulting oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-95023b1574284f0d8f51d8af64c97ca6
Source dataset
uspto-grants-2003_12
Patent number
US06670498B2

Linked notes

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