Diethyl Ether → Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

HRID 726446

반응식

HRID 726446 반응식
[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]

참가 물질

4

반응물 3

HCID 3283Diethyl EtherHCID 7294Methyl AcrylateHCID 7612Cyclopentadiene

생성물 1

HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

실험 절차

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.

후처리

  1. customThe ice bath is removed
  2. customThe solvent, unreacted methyl acrylate, and cyclopentadiene are removed at ambient temperature at reduced pressure
  3. distillationas less material distilled out of the mixture the pressure
  4. additionThe desired epimeric mixture of methyl carboxylates
  5. distillationis distilled at 42°-43°

출처 및 근거

ORD 기록
ord-aea44e4176e348358cf8d2cd257d865a
출처 데이터셋
uspto-grants-1998_01
특허 번호
USRE035717

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