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

HRID 1373767노트

반응식

HRID 1373767 반응식
[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]

참가 물질

6

반응물 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 178526657HCID 178526657, 화합물

생성물 1

HCID 210753722-(Allyloxy)-5-chloro-3-nitropyridine수율 16.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0fa675ad2edc4d09a2be2e8ea6a94f23
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163939B2

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