Sodium Bicarbonate → 6-Benzyloxy-2-(4-benzyloxyphenyl)-1-ethylindolizine

HRID 1422076노트

반응식

HRID 1422076 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH3:17])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:35]=[CH:34][C:29]([C:30](=O)[CH2:31]Br)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH:31]=[C:30]([C:29]3[CH:34]=[CH:35][C:26]([O:25][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:27][CH:28]=3)[C:15]=2[CH2:16][CH3:17])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneHCID 187069675-Benzyloxy-2-n-propylpyridine

생성물 1

HCID 187070166-Benzyloxy-2-(4-benzyloxyphenyl)-1-ethylindolizine수율 78.7%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

5-Benzyloxy-2-n-propylpyridine (50.15 g, 221 mmol) and 4-benzyloxyphenacylbromide (67.34 g, 221 mmol) was dissolved in 400 ml of dry acetone under a nitrogen atmosphere. The mixture was heated to reflux for 5 days. The reaction was cooled to room temperature and the solvent was removed. The remaining quaternary salt was suspended in 250 ml of water and 250 ml of diethyl ether and filtered off. The dried salt was suspended in 600 ml of water and sodium hydrogen carbonate (74 g, 884 mmol) was added. The mixture was refluxed for 3 days. The resulting precipitate was filtered off, washed with water and dried to afford 75.38 g (78%) of 6-benzyloxy-2-(4-benzyloxyphenyl)-1-ethylindolizine as brown crystals. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.10 (t, 3H); 2.79 (q, 2H); 5.02 (s, 2H); 5.12 (s, 2H); 6.52 (dd, 1H); 7.08 (d, 2H); 7.29-7.51 (m, 14H); 7.96 (s, 1H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 days
  3. customthe solvent was removed
  4. filtration250 ml of diethyl ether and filtered off
  5. temperatureThe mixture was refluxed for 3 days
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with water
  8. customdried

출처 및 근거

ORD 기록
ord-233019f78ace43bfa337e53ac350218b
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06080754

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