4-Pyridinecarboxaldehyde → HCID 86654331、化合物

HRID 38069ノート

反応式

HRID 38069 の反応式
COP([CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)(=O)OC.[H-].[Na+].[N:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1>C1COCC1>[N+:21]([C:17]1[CH:16]=[C:15]([C:7]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:32][C:29]2[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=2)[CH:20]=[CH:19][CH:18]=1)([O-:23])=[O:22]

参加物

5

反応物 3

HCID 133894-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 86654330HCID 86654330、化合物

生成物 1

HCID 86654331HCID 86654331、化合物収率 110%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

[(3-Nitro-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-phosphonic acid dimethyl ester (40.7 g, 0.105 mol) was dissolved in dry THF (1 L) under nitrogen. Sodium hydride (60% suspension in mineral oil)(6.3 g, 0.158 mol, 1.5 eq) was added and the mixture was stirred for 10 minutes at room temperature. Neat 4-picolinaldehyde (10 mL, 0.105 mol, 1 eq) was then added dropwise and the mixture was heated to 60° C. and stirred at this temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure to ⅓ of the original volume and then diluted with water (500 mL). pH was adjusted to 7-8 by adding a saturated solution of NaHCO3 and the mixture was extracted with ethyl acetate (4×300 mL). The organic layer was dried over Na2SO4 and concentrated to dryness. An oil (37.7 g) was obtained, which was used without further purification in the following step.

後処理

  1. temperaturethe mixture was heated to 60° C.
  2. stirringstirred at this temperature for 2.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiondiluted with water (500 mL)
  5. additionby adding a saturated solution of NaHCO3
  6. extractionthe mixture was extracted with ethyl acetate (4×300 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-1ed9a3113e1149618896a4299f0ad5c9
出典データセット
uspto-grants-2013_09
特許番号
US08524707B2

反応ノート

読み込み中…