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

HRID 466822

反応式

HRID 466822 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 189543585-(2-Iodophenyl)-2-triphenylmethyltetrazole収率 44.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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,

後処理

  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

出典と根拠

ORDレコード
ord-8c63c4fd92044c4b84daf7e2e491b3be
出典データセット
uspto-grants-1992_10
特許番号
US05157040

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