Benzophenone → 2(1-Methyltetrazol-5-yl)-1,1-diphenylethanol

HRID 1199223노트

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HRID 1199223 반응식
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[N:3]1.C([Li])CCC.[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH3:1][N:2]1[C:6]([CH2:7][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:20])=[N:5][N:4]=[N:3]1

참가 물질

5

반응물 3

HCID 3102BenzophenoneHCID 788251,5-DimethyltetrazoleHCID 178418339Butyllithium

생성물 1

HCID 147240362(1-Methyltetrazol-5-yl)-1,1-diphenylethanol수율 22%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A solution of 1,5-dimethyltetrazole (20 g; 0.204 mole) in dry THF (200 mL) was cooled to -78° C. and treated with n-butyllithium (91 mL of 2.5 molar solution in hexane; 0.227 mole) and the mixture stirred at -78° C. for 30 minutes. Benzophenone (31.1 g; 0.171 mole) was added and the mixture stirred at -78° C. for 30 minutes and allowed to warm up to 23° C. and stirred for 15 hours. The mixture was quenched with 2N HCl (100 mL) and extracted with EtOAc (3×150 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was crystallized from EtOAc-Hexane to afford the title compound as a white solid (10.5 g; 22%); m.p.=175°-176° C. (crystallized from EtOAc-hexane). MS (CI): m/e=281 for (M+H)+ ;

후처리

  1. stirringthe mixture stirred at -78° C. for 30 minutes
  2. temperatureto warm up to 23° C.
  3. stirringstirred for 15 hours
  4. customThe mixture was quenched with 2N HCl (100 mL)
  5. extractionextracted with EtOAc (3×150 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customevaporated
  8. customThe residue was crystallized from EtOAc-Hexane

출처 및 근거

ORD 기록
ord-27b91dfc37f04f08aa342bc326f8c5e4
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04898949

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