1,8-Diazabicyclo(5.4.0)undec-7-ene → E-4-Pentyloxy-1-[4-(1-imidazolylmethyl)phenyl]but-1-en-3-one

HRID 978413노트

반응식

HRID 978413 반응식
[O:1]=[C:2]([CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3]P(OC)(=O)OC.[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[CH2:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.C1CCN2C(=NCCC2)CC1>C(COC)OC>[CH2:12]([O:11][CH2:10][C:2](=[O:1])/[CH:3]=[CH:27]/[C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C:18]2[NH:19][CH:20]=[CH:21][N:17]=2)=[CH:30][CH:29]=1)[CH2:13][CH2:14][CH2:15][CH3:16]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13590432Dimethyl 2-oxo-3-pentyloxypropanephosphonateHCID 867414844-(1-Imidazolylmethyl)benzaldehyde

생성물 1

HCID 86741483E-4-Pentyloxy-1-[4-(1-imidazolylmethyl)phenyl]but-1-en-3-one

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

2 g (7.93 mmol) of dimethyl 2-oxo-3-pentyloxypropanephosphonate, 1.7 g (9.13 mmol) of 4-(1-imidazolylmethyl)benzaldehyde and 1.33 g (8.74 mmol) of DBU were stirred in 150 ml of dimethoxyethane at room temperature for 31 h. The mixture was filtered through silica gel and the solvent was removed from the filtrate in vacuo. Chromatography on silica gel (chloroform/methanol/25% aqueous NH3 =20/1/0.2) produced 1.5 g (4.80 mmol, 60%) as a yellowish oil which solidified in the refrigerator, melting point 35°-36° C.

후처리

  1. filtrationThe mixture was filtered through silica gel
  2. customthe solvent was removed from the filtrate in vacuo
  3. customChromatography on silica gel (chloroform/methanol/25% aqueous NH3 =20/1/0.2) produced 1.5 g (4.80 mmol, 60%) as a yellowish oil which

출처 및 근거

ORD 기록
ord-bcb062ab8c9a428d8fb8f11a8dea4f19
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04665080

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