Allyl Alcohol → furo[3,2-b]pyridin-3(2H)-one

HRID 1846232노트

반응식

HRID 1846232 반응식
[CH2:1]([O:4][C:5]1[C:6](Br)=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=C.N(C(OCC)=O)=NC(OCC)=[O:15].BrC1C(O)=CC=CN=1.C(O)C=C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.C([O-])(O)=O.[Na+]>[O:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2](=[O:15])[CH2:1]1

참가 물질

8

반응물 5

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 230702-Bromo-3-pyridinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23028574Pyridine, 2-bromo-3-(2-propenyloxy)-

생성물 1

HCID 14199079furo[3,2-b]pyridin-3(2H)-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
50 °C

실험 절차

3-(allyloxy)-2-bromopyridine. Diethyl azodicarboxylate (1 eq.) is added dropwise to a stirring mixture of 2-bromo-3-hydroxypyridine (0.92 eq,), allyl alcohol (0.92 eq), and PPh3 (1.1 eq) in THF (0.2 M) at 0° C. under a N2 atmosphere. The reaction mixture is warmed to 50° C. in an oil bath. Reaction progress is monitored by TLC until judged complete. The reaction mixture is cooled to ambient temperature and diluted with saturated NaHCO3 solution. The aqueous solution is extracted with EtOAc, and the organic layer is dried over Na2SO4 and concentrated. The product that may be thus obtained is purified by column chromatography to afford the title compound.

후처리

  1. customReaction progress
  2. temperatureThe reaction mixture is cooled to ambient temperature
  3. extractionThe aqueous solution is extracted with EtOAc
  4. dry with materialthe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. customThe product that may be thus obtained
  7. customis purified by column chromatography

출처 및 근거

ORD 기록
ord-3ab00b8297804d19afbc1f032ca3aa75
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952009B2

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