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

HRID 1846232ノート

反応式

HRID 1846232 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3ab00b8297804d19afbc1f032ca3aa75
出典データセット
uspto-grants-2015_02
特許番号
US08952009B2

反応ノート

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