Dimethyl Sulfoxide → 7-Benzo[1,3]dioxol-5-yl-7-pyridin-3-yl-hept-6-enoic acid

HRID 845737Notes

Reaction equation

HRID 845737 reaction equation
[OH-].[Na+].CS(C)=O.[Br-].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[CH2:35]1[O:51][C:50]2[CH:49]=[CH:48][C:39]([C:40]([C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=O)=[CH:38][C:37]=2[O:36]1>O1CCCC1.O>[CH2:35]1[O:51][C:50]2[CH:49]=[CH:48][C:39](/[C:40](/[C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=[CH:15]/[CH2:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])=[CH:38][C:37]=2[O:36]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 13285824(2H-1,3-Benzodioxol-5-yl)(pyridin-3-yl)methanone

Product 1

HCID 132858317-Benzo[1,3]dioxol-5-yl-7-pyridin-3-yl-hept-6-enoic acidYield 24.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

Sodium hydroxide (1 g, 60% in oil) was added to dimethyl sulfoxide (25 ml) under nitrogen and the mixture was heated at 85° C. with stirring for an hour. The reaction mixture was cooled to room temperature and 5-carboxypentyltriphenylphosphonium bromide (5.2 g, 11 mmoles) was added gradually. The mixture was stirred for 10 minutes and a solution of 3-(3,4-methylenedioxybenzoyl)pyridine (2.5 g, 0.11 mole) in tetrahydrofuran (10 ml) was added dropwise thereto. After completion of addition, the mixture was further stirred at room temperature for 30 minutes. After completion of the reaction, water (100 ml) was added and the neutral substance was extracted twice with toluene (50 ml). The aqueous layer was adjusted to pH 5.5 with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate as the eluent. The eluant was concentrated and the residue was crystallized from ethyl acetate-isopropyl ether to give (Z)-7-(3,4-methylenedioxyphenyl)-7-(3-pyridyl)-6-heptenoic acid (0.4 g, 24.6%). Mp 90°-91° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred for 10 minutes
  3. additionAfter completion of addition
  4. stirringthe mixture was further stirred at room temperature for 30 minutes
  5. additionwas added
  6. extractionthe neutral substance was extracted twice with toluene (50 ml)
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated under reduced pressure
  11. concentrationThe eluant was concentrated
  12. customthe residue was crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-a714585a2434449282811d16e2a865e6
Source dataset
uspto-grants-1988_07
Patent number
US04760068

Reaction notes

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