Allyl Alcohol → 2-(Allyloxy)-5-chloro-3-nitropyridine

HRID 1373767ノート

反応式

HRID 1373767 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[CH:12]1[CH:17]=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=C[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C=C>C1COCC1>[CH2:17]([O:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)[CH:12]=[CH2:13]

参加物

6

反応物 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 178526657HCID 178526657、化合物

生成物 1

HCID 210753722-(Allyloxy)-5-chloro-3-nitropyridine収率 16.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 5-chloro-3-nitro-pyridin-2-ol (0.600 g, 3.4 mmol), DBAD (1.19 g, 5.16 mmol), triphenylphosphine-polymer supported (3 mmol/g, 1.70 g, 5.16 mmol) in THF (18 mL) was added allyl alcohol (0.42 mL, 6.12 mmol). The reaction mixture was stirred at room temperature overnight, filtered through celite, and concentrated. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (95:5 to 1:1) to give 0.120 g (15%) of the desired product. MS (DCI/NH3) m/z: 214.9 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 5.01 (ddd, J=5.34, 1.40, 1.40 Hz, 2 H) 5.32 (dd, J=10.51, 1.36 Hz, 1 H) 5.49 (dd, J=17.12, 1.53 Hz, 1 H) 6.06 (m, 1 H) 8.28 (d, J=2.37 Hz, 1 H) 8.34 (d, J=2.37 Hz, 1 H).

後処理

  1. filtrationfiltered through celite
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with hexane/ethyl acetate (95:5 to 1:1)

出典と根拠

ORDレコード
ord-0fa675ad2edc4d09a2be2e8ea6a94f23
出典データセット
uspto-grants-2007_01
特許番号
US07163939B2

反応ノート

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