Dibutyltin oxide → 5-(3-Benzyloxy-benzyl)-1,2,3,4-tetrazole

HRID 902608

反応式

HRID 902608 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:22]=[N+:23]=[N-:24])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH2:15][C:16]1[NH:24][N:23]=[N:22][N:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 5198313-Benzyloxyphenylacetonitrile

生成物 1

HCID 1784203945-(3-Benzyloxy-benzyl)-1,2,3,4-tetrazole

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a stirring solution of 3-benzyloxyphenylacetonitrile (2.0 g, 8.95 mmol) in toluene (17 ml) was added trimethylsilylazide (2.37 g, 17.9 mmol) and di-n-butyltin oxide (0.22 g, 0.9 mmol). The mixture was heated at 110° C. for 48 h, and was concentrated. The reaction mixture was dissolved in ethyl acetate (100 ml) and washed two times with 10% aqueous sodium bicarbonate. The basic extracts were acidified to pH<2 with conc. HCl, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. The crude product (2.0 g, 89%) was used in the next step without further purification. MS (ESI) 267.0 (M+H+).

後処理

  1. concentrationwas concentrated
  2. dissolutionThe reaction mixture was dissolved in ethyl acetate (100 ml)
  3. washwashed two times with 10% aqueous sodium bicarbonate
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product (2.0 g, 89%) was used in the next step without further purification

出典と根拠

ORDレコード
ord-7cab76fffd884cd9a77fdd4960ec9208
出典データセット
uspto-grants-2008_04
特許番号
US07365085B2

関連ノート

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