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

HRID 15146

反応式

HRID 15146 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-742c063ba1dd404b9d9cadda52cd5a7c
出典データセット
uspto-grants-2010_06
特許番号
US07732460B2

関連ノート

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