1,4-Dioxane → HCID 17966004, compound

HRID 1484824Notes

Reaction equation

HRID 1484824 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Cl[C:12]1[C:17]([CH2:18][OH:19])=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)(O)[O-].[Na+].O1CCOCC1>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[C:17]([CH2:18][OH:19])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 2763647(2-Chloropyridin-3-yl)methanol

Product 1

HCID 17966004HCID 17966004, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of (3-chlorophenyl)boronic acid (1.6 g, 10.23 mmol, 1.20 equiv), (2-chloropyridin-3-yl)methanol (1 g, 6.97 mmol, 1.00 equiv), Pd(dppf)Cl2 (570 mg, 0.78 mmol, 0.10 equiv), and sodium bicarbonate (1.7 g, 20.24 mmol, 3.00 equiv) in a solvent mixture of dioxane (10 mL) and water (10 mL). The resulting solution was stirred for 3 h at 70° C., and then it was diluted with 20 mL of H2O. The resulting solution was extracted with 2×20 mL of dichloromethane, and the combined organic layers were concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100-1:5) as eluent to yield 1.2 g (78%) of [2-(3-chlorophenyl)pyridin-3-yl]methanol as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 2×20 mL of dichloromethane
  3. concentrationthe combined organic layers were concentrated under vacuum

Sources & evidence

ORD record
ord-de0864659bbf4926b21d32d3d7f341f1
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

Loading…