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

HRID 902608

반응식

HRID 902608 반응식
[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

참가 물질

5

반응물 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 5198313-Benzyloxyphenylacetonitrile

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-7cab76fffd884cd9a77fdd4960ec9208
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365085B2

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