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

HRID 1422076ノート

反応式

HRID 1422076 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-233019f78ace43bfa337e53ac350218b
出典データセット
uspto-grants-2000_06
特許番号
US06080754

反応ノート

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