Pyridine → HCID 58951846, compound

HRID 254599Notes

Reaction equation

HRID 254599 reaction equation
[CH2:1]([C:3]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH:5]=[O:6])[CH3:2].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:12]([C:7]1[CH:8]=[C:9]([O:11][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[C:3]([CH2:1][CH3:2])[C:4]=1[CH:5]=[O:6])[CH3:13]

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 54206997HCID 54206997, compound

Product 1

HCID 58951846HCID 58951846, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared using methodology described in Tetrahedron Lett 1998, 39, 2937-2940. To a solution of 1.50 g (8.42 mmol) 2,6-diethyl-4-hydroxy-benzaldehyde in 60 ml dichloromethane were added 1.64 g (13.5 mmol) phenylboronic acid, 2.29 g (12.6 mmol) copper(II) acetate, 30 g 4 Å molecular sieves and 4.06 ml (50.5 mmol) pyridine. The reaction mixture was stirred at room temperature for 72 h and then filtered through celite. The filtrate was extracted with 1 N aqueous hydrochloric acid, the phases were separated, and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient) to afford 1.64 g (77%) of the title compound as a yellow oil. 1H-NMR (CDCl3): 1.22 (6H, t, CH3), 2.95 (4H, q, CH2), 6.69 (2H, s, ArH), 7.08 (2H, d, ArH), 7.20 (1H, t, ArH), 7.39 (2H, dd, ArH), 10.5 (1H, s, CHO).

Workup

  1. customThis compound was prepared
  2. filtrationfiltered through celite
  3. extractionThe filtrate was extracted with 1 N aqueous hydrochloric acid
  4. customthe phases were separated
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-8cae7493f88a4398ba530a30ae6be292
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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