Borane → 6-(2-hydroxyethyl)-3-methyloxazolo[4,5-b]pyridin-2(3H)-one

HRID 964015

Reaction equation

HRID 964015 reaction equation
B.CC(C(C)C)=C.[CH3:8][N:9]1[C:13]2=[N:14][CH:15]=[C:16]([CH:18]=[CH2:19])[CH:17]=[C:12]2[O:11][C:10]1=[O:20].C(B)(C(C)C)(C)C.[OH-:28].[Na+]>O1CCCC1.O>[OH:28][CH2:19][CH2:18][C:16]1[CH:17]=[C:12]2[O:11][C:10](=[O:20])[N:9]([CH3:8])[C:13]2=[N:14][CH:15]=1

Participants

8

Reactant 5

HCID 6331BoraneHCID 112492,3-Dimethyl-1-buteneHCID 14798Sodium HydroxideHCID 5326179InChI=1/C6H15B/c1-5(2)6(3,4)7/h5H,7H2,1-4HHCID 190792863-methyl-6-vinyloxazolo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 190793176-(2-hydroxyethyl)-3-methyloxazolo[4,5-b]pyridin-2(3H)-oneYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of boron hydride (1M in tetrahydrofuran) (5 ml, 5 mmol) is cooled using a salt/ice bath, and then 2,3-dimethyl-1-butene (0.6 ml, 5 mmol) are slowly added. The temperature of the solution is increased to 0° C. and stirring is maintained for a further 2 hours at that temperature. 3-methyl-6-vinyloxazolo[4,5-b]pyridin-2(3H)-one (1.14 mg, 5 mmol) dissolved in tetrahydrofuran (20 ml) is added to the previously prepared solution of thexylborane. The whole is stirred at 0° C. for 2 hours, then a 10% aqueous sodium hydroxide solution (2.40 ml) and also oxygenated water (2.00 ml) are added in succession. After 1 hour's stirring at room temperature and evaporation of the solvent under reduced pressure, the residue is taken up in water. Extraction is carried out with dichloromethane; the organic phase is dried over magnesium sulfate and filtered, and then the solvent is evaporated off under reduced pressure. Purification by flash chromatography on silica gel (eluant: dichloromethane/methanol: 95/5) yields 6-(2-hydroxyethyl)-3-methyloxazolo[4,5-b]pyridin-2(3H)-one in a yield of 78%.

Workup

  1. temperatureis maintained for a further 2 hours at that temperature
  2. stirringThe whole is stirred at 0° C. for 2 hours
  3. stirringAfter 1 hour's stirring at room temperature
  4. customevaporation of the solvent under reduced pressure
  5. extractionExtraction
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is evaporated off under reduced pressure
  9. customPurification by flash chromatography on silica gel (eluant: dichloromethane/methanol: 95/5)

Sources & evidence

ORD record
ord-39ea5d17b9744646b760e50c6526fb59
Source dataset
uspto-grants-1998_06
Patent number
US05767128

Linked notes

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