Imidazole → HCID 58880249, 화합물

HRID 1445554노트

반응식

HRID 1445554 반응식
[Cl:1][C:2]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CN=C1.[C:21]1(=[O:26])[CH2:25][CH2:24][CH:23]=[CH:22]1>CO.O>[Cl:1][C:2]1[C:3]([CH:4]([OH:5])[C:22]2[C:21](=[O:26])[CH2:25][CH2:24][CH:23]=2)=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][N:9]=1

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 135882-Cyclopenten-1-oneHCID 32325682-Chloro-5-phenylnicotinaldehyde

생성물 1

HCID 58880249HCID 58880249, 화합물수율 95%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

The clear solution of 2-Chloro-5-phenylnicotinaldehyde (10 mmol, 2.17 g) and imidazole (10 mmol) in 50 ml. of MeOH was slowly charged with 50 ml. of deionized water. To a stirred homogeneous reaction mixture was added 2-cyclopenten-1-one (10.2 mmol., 0.88 g) at room temperature and reaction progress was monitored by TLC. Upon completion of the reaction, excess MeOH was removed under reduced pressure, washed with water and extracted with CHCl3 thrice. Combined organic layers were washed with brine solution twice. The organic layer was concentrated and column chromatography of the crude product on silica gel, using 30% EtOAC in hexane as eluent, gave pure Baylis-Hillman adduct in 95% yield (2.84 g).

후처리

  1. customreaction progress
  2. customwas removed under reduced pressure
  3. washwashed with water
  4. extractionextracted with CHCl3 thrice
  5. washCombined organic layers were washed with brine solution twice
  6. concentrationThe organic layer was concentrated
  7. customgave pure Baylis-Hillman adduct in 95% yield (2.84 g)

출처 및 근거

ORD 기록
ord-578e926ea94144febd531144d21848ae
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666883B2

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