(2,3-Dihydro-[1,4]dioxino[2,3-B]pyridin-6-YL)methanol → 2H,3H-[1,4]dioxino[2,3-b]pyridine-6-carbaldehyde

HRID 1913436

반응식

HRID 1913436 반응식
[O:1]1[C:10]2[C:5](=[N:6][C:7]([CH2:11][OH:12])=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[O:1]1[C:10]2[C:5](=[N:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1

참가 물질

4

반응물 1

HCID 21873716(2,3-Dihydro-[1,4]dioxino[2,3-B]pyridin-6-YL)methanol

생성물 1

HCID 218737862H,3H-[1,4]dioxino[2,3-b]pyridine-6-carbaldehyde수율 69.2%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매2회HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of (2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)methanol (24 g, 0.14 mol) in anhydrous CH2Cl2 (500 mL) was added activated MnO2 (25.0 g, 0.28 mol) at 0° C. in portions. The mixture was stirred at room temperature for 5 hours and another batch of activated MnO2 (25.0 g, 0.28 mol) was added in identical fashion. The mixture was stirred at room temperature overnight. The mixture was filtered through a Celite® pad and the filtrate was concentrated. The residue was purified via column chromatography (silica gel, EtOAc/petroleum ether 1:15 to 1:10) to yield 2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-6-carbaldehyde (16.0 g, 67%) as a yellow solid. MS (ES+) 166.2 (M+H)+. 1H NMR δ (CDCl3) 4.40 (s, 2H), 4.91 (s, 2H), 7.37 (d, 1H), 7.61 (d, 1H), 9.65 (s, 1H).

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationThe mixture was filtered through a Celite® pad
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified via column chromatography (silica gel, EtOAc/petroleum ether 1:15 to 1:10)

출처 및 근거

ORD 기록
ord-aba5c4583706474d8cad793ab232255f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609680B2

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