Sodium Thiosulfate → 3-Allyloxy-pyridine-2-carbaldehyde

HRID 250942ノート

反応式

HRID 250942 の反応式
[CH2:1]([O:4][C:5]1[C:6]([CH2:11][OH:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:4][C:5]1[C:6]([CH:11]=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

参加物

6

反応物 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 14598977(3-Allyloxy-pyridin-2-yl)-methanol

生成物 1

HCID 450909933-Allyloxy-pyridine-2-carbaldehyde収率 98.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (3-allyloxy-pyridin-2-yl)-methanol (2.08 g, 12.6 mmol) (Chen, Y. L. Eur. Pat. Appl. (1985), EP 150984) in CH2Cl2 (60 mL) was added Dess-Martin Periodinane (5.82 g, 13.7 mmol), and stirred at room temperature for 24 hours. CH2Cl2 (40 mL), saturated NaHCO3 (30 mL), and aqueous sodium thiosulfate (30 mL) were added and stirred for 40 minutes. The layers were separated and the aqueous phase was extracted with CH2Cl2 (2×50 mL). The combined organic extracts were washed with brine (1×75 mL), dried (Na2SO4), and concentrated to provide 2.02 g (98%) of 3-allyloxy-pyridine-2-carbaldehyde as a brown oil. 1H NMR (CDCl3) δ 4.71 (d, 2H, J=6.0 Hz), 5.37 (d, 1H, J=12.0 Hz), 5.50 (d, 1H, J=18.0 Hz), 5.99-6.12 (m, 1H), 7.38-7.48 (m, 2H), 8.40 (d, 1H, J=3.0 Hz), 10.41 (s, 1H).

後処理

  1. stirringstirred for 40 minutes
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (2×50 mL)
  4. washThe combined organic extracts were washed with brine (1×75 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-907f21e5df2c46b1ae1bf9c3040237c7
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

反応ノート

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