Toluene → HCID 13340174, compound

HRID 1249618Notes

Reaction equation

HRID 1249618 reaction equation
[C:1]1([CH:7]2[O:16][C:15]3[C:10](=[N:11][C:12]([CH:17]=O)=[CH:13][CH:14]=3)[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[C:21]1(C)C=CC=CC=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:1]1([CH:7]2[O:16][C:15]3[C:10](=[N:11][C:12]([CH:17]=[CH2:21])=[CH:13][CH:14]=3)[CH2:9][O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 137484012-Phenyl-2H,4H-[1,3]dioxino[5,4-b]pyridine-6-carbaldehyde

Product 1

HCID 13340174HCID 13340174, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

In a two liter 3-neck, round bottom flask, fitted with a mechanical stirrer, a thermometer and a reflux condenser, a heterogeneous mixture of 2-phenyl-4H-1,3-dioxino[5,4-b]pyridine-6-carbaldehyde (24.1 g., 0.1 mole) sodium hydroxide (24.0 g., 0.6 mole) and methyltriphenylphosphonium bromide (71.5 g., 0.2 mole) in toluene (200 ml.) and water (600 ml.) was stirred at room temperature for 24 hours. The toluene layer was separated and the aqueous layer was washed with toluene (100 ml.). The combined toluene layers were dried over anhydrous magnesium sulfate. The toluene solution was then passed through a 10 mm. pad of silica gel which was then washed with 1 liter of ether/hexane solution (v/v 3:2). Evaporation of the solvents on a rotary evaporation in vacuo gave the crystalline 2-phenyl-6-vinyl-4H-1,3-dioxino[5,4-b]pyridine, 14.3 g. (59%); m.p. 54°-57° C.; mass spec (70 eV) m/e 211 (M+), 134, 133, 132, 106, 105, 104.

Workup

  1. customIn a two liter 3-neck, round bottom flask, fitted with a mechanical stirrer
  2. customThe toluene layer was separated
  3. washthe aqueous layer was washed with toluene (100 ml.)
  4. dry with materialThe combined toluene layers were dried over anhydrous magnesium sulfate
  5. washpad of silica gel which was then washed with 1 liter of ether/hexane solution (v/v 3:2)
  6. customEvaporation of the solvents
  7. customon a rotary evaporation in vacuo

Sources & evidence

ORD record
ord-b901cae111e9427e8a6b1fd7d2db39c5
Source dataset
uspto-grants-1986_12
Patent number
US04632992

Reaction notes

Loading…