Iodine → 5-(2-Iodophenyl)-2-triphenylmethyltetrazole

HRID 466822

반응식

HRID 466822 반응식
[C:1]1([C:7]2[N:8]=[N:9][N:10]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[I:42]I>C1COCC1>[I:42][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:7]1[N:8]=[N:9][N:10]([C:12]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:11]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 8058HexaneHCID 32929595-Phenyl-2-trityltetrazoleHCID 178418339Butyllithium

생성물 1

HCID 189543585-(2-Iodophenyl)-2-triphenylmethyltetrazole수율 44.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

To a solution of 0.5 g (1.3 mmoles) of 18a in 10 mL dry THF cooled to -20° C. under a nitrogen atmosphere was added dropwise with stirring 0.55 mL of 2.5M n-butyl lithium in hexane (1.4 mmoles). When addition was complete, the reaction was allowed to warm to -10° C. over one hour, held there one hour, then cooled to -78° C. After stirring a few minutes, 0.4 g (1.57 mmole) of I2 was added all at once, and stirring continued. After 1 hour the reaction mixture was allowed to warm to ambient temperature. After removal of the solvent, the residue was partitioned between CHCl3 and 1M KH2PO4. The aqueous phase was extracted two more times, the combined organic phases washed with sufficient aqueous Na2S2O3 to remove excess I2, dried (MgSO4) and the solvent evaporated. The residue was crystallized from CH2Cl2 /ether to give 0.3 g product,

후처리

  1. additionwas added dropwise
  2. additionWhen addition
  3. temperaturecooled to -78° C
  4. stirringstirring
  5. waitAfter 1 hour the reaction mixture was allowed
  6. temperatureto warm to ambient temperature
  7. customAfter removal of the solvent
  8. customthe residue was partitioned between CHCl3 and 1M KH2PO4
  9. extractionThe aqueous phase was extracted two more times
  10. washthe combined organic phases washed with sufficient aqueous Na2S2O3
  11. customto remove excess I2
  12. dry with materialdried (MgSO4)
  13. customthe solvent evaporated
  14. customThe residue was crystallized from CH2Cl2 /ether

출처 및 근거

ORD 기록
ord-8c63c4fd92044c4b84daf7e2e491b3be
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05157040

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