Diethyl Ether → Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate
Reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]([O:10][CH3:11])(=[O:9])C=C.[CH3:12][CH2:13]OCC>>[CH:2]12[CH2:1][CH:5]([CH:12]=[CH:13]1)[CH2:4][CH:3]2[C:6]([O:10][CH3:11])=[O:9]Participants
4
Procedure
In 100 ml of anhydrous ether at 0° C. is mixed 30 ml of cyclopentadiene and 32 ml of methyl acrylate. The ice bath is removed and the mixture allowed to stir overnight. The solvent, unreacted methyl acrylate, and cyclopentadiene are removed at ambient temperature at reduced pressure; as less material distilled out of the mixture the pressure is gradually reduced to 0.5 mm. The desired epimeric mixture of methyl carboxylates is distilled at 42°-43° and 0.5 mm; ir: 3118, 3060, 2965, 2941, 2862, 1734, 1428, 1329, 1264, 1190, 1024, 704, cm-1 ; 60 MHz NMR: endo/exo=80/20.
Workup
- customThe ice bath is removed
- customThe solvent, unreacted methyl acrylate, and cyclopentadiene are removed at ambient temperature at reduced pressure
- distillationas less material distilled out of the mixture the pressure
- additionThe desired epimeric mixture of methyl carboxylates
- distillationis distilled at 42°-43°
Sources & evidence
- ORD record
- ord-92170fa1fd29492488edc107994fd7e3
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04689380
Reaction notes
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