Potassium Carbonate → 2-{4-[2-(1,3-Dioxolan-2-yl)vinyl]-phenyl)pyridine

HRID 1927646Notes

Reaction equation

HRID 1927646 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[Br-].[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOCCN(CCOCCOC)CCOCCOC.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[CH:21]=[CH:11][C:10]1[CH:13]=[CH:14][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 15152404-Pyridin-2-ylbenzaldehydeHCID 2724194(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide

Product 1

HCID 686730972-{4-[2-(1,3-Dioxolan-2-yl)vinyl]-phenyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-pyridyl)benzaldehyde (6.0 g, 32.8 mmol), (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (18.3 g, 42.6 mmol), tris[2-(2-methoxyethoxy)ethyl]amine (13.76 g, 42.6 mmol), dichloromethane (200 mL) and saturated potassium carbonate (200 mL) was heated to reflux overnight. The reaction was cooled to rt and the product was extracted with ethyl acetate-hexanes (2×). The extracts were washed with water and brine, and concentrated to afford 2-{4-[2-(1,3-dioxolan-2-yl)vinyl]-phenyl)pyridine, which was dissolved in methanol (120 mL) and was stirred with Pd on carbon (10%, 1.75 g) under 1 atmosphere of hydrogen overnight. The reaction mixture was filtered through Celite, and the filtrate was concentrated to afford crude 2-{4-[2-(1,3-dioxolan-2-yl)ethyl]phenyl}pyridine, which was dissolved in acetone (80 mL) and treated with 4 M HCl (aq., 80 mL). After stirring at rt for 20 h, the product was extracted with ethyl acetate-hexanes (2×). The extracts were washed with water and brine, and concentrated, and the residue was purified on silica gel eluted with a 5-100% ethyl acetate in hexanes to afford the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. extractionthe product was extracted with ethyl acetate-hexanes (2×)
  4. washThe extracts were washed with water and brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-378a1c44cd5a4517aa4ba4a7fa44f3ad
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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