2-Pyridinecarboxaldehyde → E-3-(1,3-dioxan-2-yl)-1-(2-pyridyl)-1-propene

HRID 53564

Reaction equation

HRID 53564 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[Br-].O1CCCOC1CC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.N1C=CC=CC=1C=O>C1COCC1.O>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7]/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7]/[CH:8]=[CH:9]\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

8

Reactant 4

HCID 142732-PyridinecarboxaldehydeHCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 539232753-(1,3-Dioxan-2-yl)-1-(2-pyridyl)-1-propeneHCID 178418339Butyllithium

Product 2

HCID 19694130E-3-(1,3-dioxan-2-yl)-1-(2-pyridyl)-1-propeneHCID 70113689Z-3-(1,3-dioxan-2-yl)-1-(2-pyridyl)-1-propene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(E and Z)-3-(1,3-Dioxan-2-yl)-1-(2-pyridyl)-1-propene (148 and 149). To a suspension of 4.6 g (10.2 mmol) of [2-(1,3-dioxan-2-yl)ethyl]triphenylphosphonium bromide (Aldrich Chemical Co.) in 50 mL of THF at 0° C. was added 6.4 mL (10.2 mmol) of n-butyl lithium (1.6M in hexanes) and the resulting red solution was allowed to stir at 0° C. for 0.5 h. To this solution was added 880 μL (9.3 mmol) of 2-pyridinecarboxaldehyde (Aldrich Chemical Co.). The reaction mixture was allowed to stir at room temperature for 1 h and was then poured into water and partitioned with ether. The combined either extracts were dried over MgSO4 and concentrated. Flash chromatography (elution with 3:1 hexane:ethyl acetate) gave 0.43 g of E-3-(1,3-dioxan-2-yl)-1-(2-pyridyl)-1 -propene (148) and 1.12 g of Z-3-(1,3-dioxan-2-yl)-1-(2-pyridyl)-1-propene (149). 1H NMRs consistent with structures.

Workup

  1. stirringto stir at room temperature for 1 h
  2. custompartitioned with ether
  3. dry with materialextracts were dried over MgSO4
  4. concentrationconcentrated
  5. washFlash chromatography (elution with 3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-321cdd4893b44debad54cad867cbe1e8
Source dataset
uspto-grants-1997_04
Patent number
US05620971

Linked notes

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