Ethanol → 3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethanol

HRID 965851ノート

反応式

HRID 965851 の反応式
Cl[C:2]1[N:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]2[CH:11]=[CH:10][CH2:9][O:8][C:7]=12.CCO.[OH-].[Na+]>[Pd]>[O:8]1[C:7]2=[CH:2][N:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]2[CH2:11][CH2:10][CH2:9]1

参加物

5

反応物 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22313337HCID 22313337、化合物

生成物 1

HCID 223133613,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethanol収率 89%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

(8-Chloro-2H-pyrano[2,3-c]pyridin-6-yl)methanol (988 mg, 5.0 mmol) is combined with 100 mg 10% Pd/C in 25 ml EtOH containing 3 ml (6 mmol) of 2N aqueous NaOH in a 250 ml PARR shaker bottle. The reaction is hydrogenated at 50 PSI for 48 h, the catalyst is removed by filtration, and the filtrate is concentrated to dryness. The mixture is partitioned between 1×10 ml 1:1 saturated NaCl/conc. NH4OH and 4×10 ml CH2Cl2 and the combined organic layer is dried (K2CO3). The mixture is concentrated in vacuo to give 730 mg (89%) of 3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethanol as an off-white solid. HRMS (FAB) calcd for C9H11NO2+H: 166.0868, found 166.0868 (M+H)+.

後処理

  1. customthe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated to dryness
  3. customThe mixture is partitioned between 1×10 ml 1:1 saturated NaCl/conc
  4. dry with materialNH4OH and 4×10 ml CH2Cl2 and the combined organic layer is dried (K2CO3)
  5. concentrationThe mixture is concentrated in vacuo

出典と根拠

ORDレコード
ord-cf223513a5b4418a99cbe25044245371
出典データセット
uspto-grants-2005_10
特許番号
US06951868B2

反応ノート

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