Water → 5-Benzyloxy-2-methoxyphenacyl 3-Pyridyl Ether

HRID 6372

Reaction equation

HRID 6372 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH:18]=1)[C:14](=[O:17])[CH2:15]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1.[H-].[Na+].O>CN(C)C=O>[N:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH2:15][C:14]([C:13]2[CH:18]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=[CH:11][C:12]=2[O:19][CH3:20])=[O:17])[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 148556125-Benzyloxy-2-methoxyphenacyl bromide

Product 1

HCID 148830005-Benzyloxy-2-methoxyphenacyl 3-Pyridyl EtherYield 25.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-benzyloxy-2-methoxyphenacyl bromide (4.0 g, 0.0119 mol) in 80 ml of dry dimethylformamide was added 3-hydroxypyridine (1.24 g, 0.013 mol, 1.1 equiv) followed by NaH (50% in oil, 0.604 g, 1.1 equiv). After stirring for 18 hours under N2, the mixture was poured into 500 ml of ice and water, and extracted 2×500 ml ethyl acetate. The organic layers were combined, washed 2×500 ml H2O and 1×300 ml brine, dried (Na2SO4), stripped to an oil, and chromatographed on silica gel using 1:1 hexane:ethyl acetate as eluant to yield 1.07 g of present title product as a solid; IR(KBr) 1670 cm-1;MS 349 (M+); 1H-NMR (300 MHz, CDCl3) delta (ppm) 3.95 (s, 3H), 5.1 (s, 2H), 5.35 (s, 2H), 2.0 (d, 1 H), 7.2-7.5 (m, 8H), 7.6 (d, 1H), 8.3 (d, 1H), 8.4 (d, 1H).

Workup

  1. extractionextracted 2×500 ml ethyl acetate
  2. washwashed 2×500 ml H2O and 1×300 ml brine
  3. dry with materialdried (Na2SO4)
  4. customchromatographed on silica gel using 1:1 hexane

Sources & evidence

ORD record
ord-8e62ba77ab194d9c9cc5595ca51f8d17
Source dataset
uspto-grants-1993_09
Patent number
US05248685

Linked notes

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