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

HRID 1600988노트

반응식

HRID 1600988 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a6709b4244e94ee1af5917c64c681f12
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977105

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