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

HRID 4521

反応式

HRID 4521 の反応式
[H-].[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

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 13285824(2H-1,3-Benzodioxol-5-yl)(pyridin-3-yl)methanone

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

Sodium hydride (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 eluate 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.

後処理

  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 eluate was concentrated
  12. customthe residue was crystallized from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-a74b6d8de3c74927ba4f80b2e8d86f3c
出典データセット
uspto-grants-1988_02
特許番号
US04727078

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