4-Toluenesulfonyl chloride → Bicyclo[2.2.2]oct-1-ylmethyl 4-methylbenzene-1-sulfonate

HRID 1600988ノート

反応式

HRID 1600988 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]12([CH2:20][OH:21])[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][CH2:13]2.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(#N)C>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:21][CH2:20][C:12]23[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]2)[CH2:14][CH2:13]3)(=[O:9])=[O:8])=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 13245694{bicyclo[2.2.2]octan-1-yl}methanol

生成物 1

HCID 280185Bicyclo[2.2.2]oct-1-ylmethyl 4-methylbenzene-1-sulfonate収率 28.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Solid para-toluenesulfonyl chloride (0.449 g) was added to a solution of bicyclo-[2,2,2]oct-1-ylmethanol (300 mg) and triethylamine (0.45 ml) in anhydrous acetonitrile (6 ml) under nitrogen. The mixture was stirred at room temperature for 16 hours then heated at reflux for 18 hours, poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ether. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ether:hexane (1:9) and further purified by preparative normal-phase HPLC on a Dynamax™ Silica column with hexane:ethyl acetate gradient elution to give the sub-title compound as an oil (0.180 g).

後処理

  1. temperaturethen heated
  2. temperatureat reflux for 18 hours
  3. extractionextracted with ether
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with ether:hexane (1:9)
  8. customfurther purified by preparative normal-phase HPLC on a Dynamax™ Silica column with hexane
  9. washethyl acetate gradient elution

出典と根拠

ORDレコード
ord-a6709b4244e94ee1af5917c64c681f12
出典データセット
uspto-grants-1999_11
特許番号
US05977105

反応ノート

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