Methyl Ethyl Ketone → 5-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)]-2-(3-bromopropyl)-2H-tetrazole

HRID 620241ノート

反応式

HRID 620241 の反応式
[Na].[OH:2][C:3]1[C:8]([CH2:9][CH2:10][CH3:11])=[C:7]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:24][N:23]=[N:22][N:21]=3)=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]=1[C:25](=[O:27])[CH3:26].[Br:28][CH2:29][CH2:30][CH2:31]Br.CCC(C)=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[C:25]([C:4]1[CH:5]=[CH:6][C:7]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:21]=[N:22][N:23]([CH2:31][CH2:30][CH2:29][Br:28])[N:24]=3)=[CH:16][CH:15]=2)=[C:8]([CH2:9][CH2:10][CH3:11])[C:3]=1[OH:2])(=[O:27])[CH3:26]

参加物

6

反応物 4

HCID 6569Methyl Ethyl KetoneHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 178439419HCID 178439419、化合物

生成物 1

HCID 144581835-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)]-2-(3-bromopropyl)-2H-tetrazole収率 82%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

1-[2-Hydroxy-3-propyl-4-((4-(1H-tetrazol-5-yl)phenoxy)methyl)phenyl]ethanone sodium salt (5 g, 0.013 mol), 1,3-dibromopropane (3.5 g, 0.18 mol), and MEK (50 ml) were combined potassium carbonate (4.15 g, 0.025 mol) potassium was added and the reaction mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The volume of the concentrate was doubled by the addition of water and the resultant solution was extracted with ethyl acetate (3×). The ethylacetate layers were combined, washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed by HPLC (preparatory-scale, silica gel column, eluted with a mixture of 9:1 toluene:ethyl acetate) to yield 5.0 g, 82% yield of the title product: n.m.r. (300 MHz CDCl3) δ: 1.0 (t, 3H); 1.6 (m, 2H); 2.6 (s and t, 5H); 2.7 (t, 2H); 3.5 (t, 2 H); 4.8 (t, 2H); 5.15 (s, 2H); 7.1 (d, 2H); d, 1H); 7.6 (d, 1H); 8.1 (d, 2H); 12.7 (s, 1H).

後処理

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionThe volume of the concentrate was doubled by the addition of water
  4. extractionthe resultant solution was extracted with ethyl acetate (3×)
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed by HPLC (preparatory-scale, silica gel column
  10. washeluted with a mixture of 9:1 toluene

出典と根拠

ORDレコード
ord-bc31ecc2e0f94eef8287d81b8fe5dc73
出典データセット
uspto-grants-1989_04
特許番号
US04820722

反応ノート

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