Ethyl Acetate → 5-(3-(2,6-Dimethylbenzyloxy)-4-methoxybenzyl)-1H-tetrazole

HRID 337252노트

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HRID 337252 반응식
[CH3:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14][C:15]#[N:16])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>CN(C=O)C.CCCCCC>[CH3:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:14][C:15]1[NH:24][N:23]=[N:22][N:16]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 669590872-(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)acetonitrile

생성물 1

HCID 1784899435-(3-(2,6-Dimethylbenzyloxy)-4-methoxybenzyl)-1H-tetrazole

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8058Hexane용매

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온도
90 °C

실험 절차

A mixture of 2-(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)acetonitrile (Step E, 2.17 g, 7.5 mmol), sodium azide (0.590 g, 9.1 mmol) and ammonium chloride (0.486 g, 9.1 mmol) in dry DMF (20 ml) was heated under argon at 90° C. for 16 hours or until all the starting material is consumed, the reaction mixture was cooled, diluted with water and extracted with EtOAc (30 ml×4). The combined organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol 95:5) to give semi solid product. The semi solid was stirred with 1:2 ethyl acetate:hexane (15 ml) for 10 minutes, and filtered to give product as a white solid.

후처리

  1. customis consumed
  2. temperaturethe reaction mixture was cooled
  3. additiondiluted with water
  4. extractionextracted with EtOAc (30 ml×4)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (chloroform:methanol 95:5)
  10. customto give semi solid product
  11. filtrationfiltered
  12. customto give product as a white solid

출처 및 근거

ORD 기록
ord-71af0bf6abef4d148a7f5693bf3fb06f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889724B2

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