Methyl iodide → 3-(Tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane

HRID 454113ノート

反応式

HRID 454113 の反応式
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)([CH3:4])([CH3:3])[CH3:2].[CH2:17]([Li])CCC.CI.[Cl-].[NH4+]>CN(C=O)C.CCOCC.C(OCC)(=O)C>[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]([CH3:17])=[N:13][CH:12]=[N:11]1)([CH3:2])([CH3:4])[CH3:3]

参加物

8

反応物 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 220308973-(Tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propaneHCID 178418339Butyllithium

生成物 1

HCID 220308553-(Tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane収率 98%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-70 °C

実験手順

To a solution of 3-(tertbutyldimethylsilyloxy)-1-(1,2,4-triazol-1-yl)propane (7 g, 29 mmol) in DMF (100 ml) cooled at −70° C. was added 2.5M n-butyllithium (17.4 ml) over 45 minutes. After stirring for 90 minutes at −70° C., methyl iodide (3.6 ml, 58 mmol) was added. After stirring for 2 hours at ambient temperature, the mixture was poured onto saturated ammonium chloride. The mixture was then diluted with ether and ethyl acetate. The organic layer was separated, washed with aqueous sodium thiosulphate followed by brine, dried (MgSO4) and evaporated to give 3-(tertbutyldimethylsilyloxy)-1-(5-methyl-[1,2,4]-triazol-1-yl)propane (7.3 g, 98%).

後処理

  1. stirringAfter stirring for 2 hours at ambient temperature
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium thiosulphate
  4. dry with materialdried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-d38978b4d4294d619f9d4a4a3c7f0456
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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