Water → HCID 54348602, compound

HRID 1030029Notes

Reaction equation

HRID 1030029 reaction equation
[Br-].[O:2]1[CH2:6][CH2:5][O:4][CH:3]1[C:7]1C=CC=CC=1[P+](C)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:27]([O:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[N:47]=[CH:46][C:45]([CH:48]=O)=[CH:44][CH:43]=2)=[CH:38][CH:37]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(=O)([O-])O.[Na+].O>C(OCC)C>[O:2]1[CH2:6][CH2:5][O:4][CH:3]1[CH:7]=[CH:48][C:45]1[CH:44]=[CH:43][C:42]([C:39]2[CH:38]=[CH:37][C:36]([O:35][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:41][CH:40]=2)=[N:47][CH:46]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 19821238HCID 19821238, compoundHCID 86745651HCID 86745651, compound

Product 1

HCID 54348602HCID 54348602, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 6.44 g of (1,3-dioxolan-2-yl)-methyl-triphenylphosphonium bromide in 70 ml of diethyl ether is treated with 1.68 g of potassium t-butylate within 5 minutes while gassing with nitrogen. The orange suspension is stirred for 30 minutes, then cooled to 0° C. and treated within 10 minutes with a solution of 3.11 g of 6-[4-(octyloxy)phenyl]-3-pyridinecarboxaldehyde (prepared in accordance with Example 2) in 25 ml of diethyl ether. The reaction mixture is stirred at room temperature for a further 3 hours and then treated with 0.6 g of sodium hydrogen carbonate and with 20 ml of water. The organic phase is washed with water, dried over sodium sulfate and concentrated. The residue is taken up in hexane and 20 ml of 80 percent aqueous methanol. The phases are separated and the hexane phase is washed with 10 ml of 80 percent methanol, dried over sodium sulfate and concentrated. Chromatographic purification of the residue on 50 g of silica gel with hexane/ethyl acetate (vol. 9:1) gives 5-[2-(1,3-dioxolan-2-yl)vinyl]-2-[4-(octyloxy)phenyl]-pyridine.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for a further 3 hours
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe phases are separated
  6. washthe hexane phase is washed with 10 ml of 80 percent methanol
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customChromatographic purification of the residue on 50 g of silica gel with hexane/ethyl acetate (vol. 9:1)

Sources & evidence

ORD record
ord-806cc7a4428944cc95b81b861f8974f7
Source dataset
uspto-grants-1992_04
Patent number
US05104569

Reaction notes

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