Triphenylphosphine → 6,7-Dihydro-2H-pyrano[2,3-c]pyridazin-3(5H)-one

HRID 15146

반응식

HRID 15146 반응식
O[CH2:2][CH2:3][CH2:4][C:5]1[C:6](=[O:12])[NH:7][NH:8][C:9](=[O:11])[CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:7]1[NH:8][C:9](=[O:11])[CH:10]=[C:5]2[CH2:4][CH2:3][CH2:2][O:12][C:6]=12

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 675266004-(3-Hydroxypropyl)-1,2-dihydro-3,6-pyridazinedione

생성물 1

HCID 675269516,7-Dihydro-2H-pyrano[2,3-c]pyridazin-3(5H)-one수율 79.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of 4-(3-hydroxypropyl)-1,2-dihydro-3,6-pyridazinedione (1.48 g, 8.7 mmol) in THF (105 ml) was held in an ultrasound bath for 5 minutes, then cooled under argon in an ice bath. Triphenylphosphine (3.67 g, 14 mmol) was added, followed by diisopropyl azodicarboxylate (2.76 ml, 14 mmol). After 30 minutes the solvent was evaporated and the residue kept under high vacuum overnight. Chromatography, eluting first with 2.5% methanol/dichloromethane until triphenylphosphine oxide was removed and then with 5% methanol/dichloromethane, gave the product as an off-white solid (1.049 g, 79%).

후처리

  1. temperaturecooled under argon in an ice bath
  2. customAfter 30 minutes the solvent was evaporated
  3. customkept under high vacuum overnight
  4. washChromatography, eluting first with 2.5% methanol/dichloromethane until triphenylphosphine oxide
  5. customwas removed

출처 및 근거

ORD 기록
ord-742c063ba1dd404b9d9cadda52cd5a7c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732460B2

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