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

HRID 53166노트

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HRID 53166 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-e08226f300284e3098a50c89a9721865
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618819

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