Methanol → HCID 45091418, compound

HRID 495424Notes

Reaction equation

HRID 495424 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)[CH:2]=C.I([O-])(=O)(=O)=[O:16].[Na+].C1COCC1.CO>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O.O>[N:13]1[C:14]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[O:4][CH2:1][CH:2]=[O:16])[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4613598-allyloxyquinolineHCID 23667635Sodium periodate

Product 1

HCID 45091418HCID 45091418, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of osmium tetroxide (2.1 mmol) in tert-butanol (26 mL) was added to a stirred mixture of 8-allyloxyquinoline (3.7 g, 20 mmol), sodium periodate (15 g, 70 mmol), THF (90 mL), methanol (4 mL) and water (2 mL). The mixture was stirred at room temperature for 20 h, then was extracted with dichloromethane (100 mL). The aqueous layer was basified with the addition of sodium hydrogen carbonate then was extracted with dichloromethane (2×200 mL). The combined organic extracts were washed with 20% w/w sodium sulfite solution (200 mL), then dried over sodium sulfate and evaporated in vacuo to give the title compound (1.1 g, 30%) as an amber oil.

Workup

  1. extractionwas extracted with dichloromethane (100 mL)
  2. additionThe aqueous layer was basified with the addition of sodium hydrogen carbonate
  3. extractionthen was extracted with dichloromethane (2×200 mL)
  4. washThe combined organic extracts were washed with 20% w/w sodium sulfite solution (200 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5f376fb813824da1847650602a200981
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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