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

HRID 965851노트

반응식

HRID 965851 반응식
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

참가 물질

5

반응물 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22313337HCID 22313337, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

(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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-cf223513a5b4418a99cbe25044245371
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951868B2

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