Tetrahydrofuran → 1-(3-Pyridyl)-3-[(4-methoxyphenyl)methoxy]propan-2-ol

HRID 845489Notes

Reaction equation

HRID 845489 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.O1CC1C[CH:16]([O:25][CH:26]([CH2:35][CH:36]1OC1)C1C=CC(OC)=CC=1)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.[O:40]1CCCC1>>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH2:36][CH:35]([OH:40])[CH2:26][O:25][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH:3]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran4×HCID 122863-BromopyridineHCID 566290762,3-Epoxypropyl-4-methoxybenzyl etherHCID 178418306HCID 178418306, compound

Product 1

HCID 135902771-(3-Pyridyl)-3-[(4-methoxyphenyl)methoxy]propan-2-ol

Procedure

3-Bromopyridine (3.5 g, 0.022 mol) in dry tetrahydrofuran (5 ml) was added dropwise to a stirred solution of t-butyllithium (1.4M, 15.7 ml, 0.022 mol) in dry tetrahydrofuran (100 ml) at -100° C. under nitrogen atmosphere. The resultant solution was stirred for 20 min and cuprous iodide-trimethyl phosphite complex (6.9 g, 0.022 mol) in dry tetrahydrofuran (15 ml) added. After a further 10 min, 2,3-epoxypropyl-4-methoxybenzyl ether (4.27 g, 0.022 mol) in dry tetrahydrofuran (10 ml) was added and the mixture allowed to warm up from -100° to 20° C. over 3 hours and left to stir overnight at room temperature. The mixture was quenched with saturated aqueous ammonium chloride and evaporated in vacuo. The solid was extracted with ethyl acetate (300 ml), washed with water and dried (MgSO4). Filtration and evaporation of solvent in vacuo gave a crude oil which was purified by column chromatography (silica gel/chloroform). Recrystallisation from ether/pentane gave pure 1-(3-pyridyl)-3-[(4-methoxyphenyl) methoxy]propan-2-ol as a colourless crystalline solid, m.p. 55°-56°.

Workup

  1. temperatureto warm up from -100° to 20° C. over 3 hours
  2. waitleft
  3. customThe mixture was quenched with saturated aqueous ammonium chloride
  4. customevaporated in vacuo
  5. extractionThe solid was extracted with ethyl acetate (300 ml)
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and evaporation of solvent in vacuo
  9. customgave a crude oil which
  10. customwas purified by column chromatography (silica gel/chloroform)
  11. customRecrystallisation from ether/pentane

Sources & evidence

ORD record
ord-d7d3e58c48e74e49b26ef8ca57566d91
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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