Triethylsilane → 4-[1-(tert-butyldimethylsilanyloxy)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

HRID 1095306ノート

反応式

HRID 1095306 の反応式
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Si:13]([O:20][CH:21]([C:50]1[CH:55]=[CH:54][C:53]([C:56]#[N:57])=[CH:52][CH:51]=1)[C:22]([O:24][CH2:25][C:26]1[N:27]=[CH:28][N:29]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=1)=O)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C([SiH](CC)CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Si:13]([O:20][CH:21]([C:50]1[CH:55]=[CH:54][C:53]([C:56]#[N:57])=[CH:52][CH:51]=1)[CH2:22][O:24][CH2:25][C:26]1[N:27]=[CH:28][N:29]([C:31]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=1)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:15])[CH3:14]

参加物

6

反応物 3

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 866329551-trityl-1H-imidazol-4-ylmethyl (tert-butyldimethylsilyloxy)(4-cyanophenyl)acetate

生成物 1

HCID 667816954-[1-(tert-butyldimethylsilanyloxy)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of 1.27 mmol of titanium tetrachloride in 1.5 ml of dichloromethane is added to a solution of 2.61 mmol of trimethylsilyl trifluoromethanesulphonate in 1 ml of dichloromethane at 0° C. The mixture is stirred at room temperature for 4 hours and then cooled to 0° C. A solution of 0.83 mmol of 1-trityl-1H-imidazol-4-ylmethyl (tert-butyldimethylsilyloxy)(4-cyanophenyl)acetate and 4.17 mmol of triethylsilane in 2 ml of dichloromethane is added, and the reaction mixture is stirred at room temperature for 20 hours. The reaction mixture is poured into ice-water and extracted with ethyl acetate (2×). The combined organic phases are washed with water and brine, dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60 F).

後処理

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture is stirred at room temperature for 20 hours
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic phases are washed with water and brine
  5. dry with materialdried with sodium sulphate
  6. customevaporated

出典と根拠

ORDレコード
ord-a2bd8ce0cfed49ae89c52f9b933aeaba
出典データセット
uspto-grants-2012_03
特許番号
US08138176B2

反応ノート

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