3,5-Dimethyl-4-(6-hydroxytetrahydropyran-2-ylethyl)-isoxazole → Racemic 7-(3,5-dimethyl-4-isoxazolyl)-5-oxo-heptanoic acid

HRID 442027

反応式

HRID 442027 の反応式
[CH3:1][C:2]1[C:6]([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH:11]([OH:15])[O:10]2)=[C:5]([CH3:16])[O:4][N:3]=1.CC1C(C=CC2CCC=CO2)=C(C)[O:20]N=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(O)[O-].[Na+]>CC(C)=O>[CH3:1][C:2]1[C:6]([CH2:7][CH2:8][C:9](=[O:20])[CH2:14][CH2:13][CH2:12][C:11]([OH:15])=[O:10])=[C:5]([CH3:16])[O:4][N:3]=1

参加物

6

反応物 4

HCID 215059703,5-Dimethyl-4-(6-hydroxytetrahydropyran-2-ylethyl)-isoxazoleHCID 23665763Sodium BisulfiteHCID 706238504-[2-(3,4-Dihydro-2H-pyran-2-yl)ethenyl]-3,5-dimethyl-1,2-oxazoleHCID 131709961Jones' reagent

生成物 1

HCID 20362373Racemic 7-(3,5-dimethyl-4-isoxazolyl)-5-oxo-heptanoic acid

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 3,5-dimethyl-4-(6-hydroxytetrahydropyran-2-ylethyl)-isoxazole, prepared as described in part B from 60.5 g. (0.294 mole) of racemic 3,5-dimethyl-4-(3,4-dihydro-2H-pyran-2-ylvinyl)-isoxazole, in 600 ml. of acetone was cooled in an ice bath as 400 ml. of Jones reagent was added dropwise over a 1.0 hr. period. The resulting suspension was stirred at room temperature overnight. Saturated sodium bisulfite solution was added to destroy the excess oxidizing agent and most of the acetone was removed at reduced pressure. The residue was diluted with water, saturated with sodium chloride, and extracted with ethyl acetate. The ethyl acetate solutions were washed with brine and then with excess saturated aqueous sodium bicarbonate solution. The sodium bicarbonate solutions were washed with ether, acidified with 3N hydrochloric acid, saturated with sodium chloride, and extracted with ethyl acetate. The ethyl acetate solutions were washed with brine and dried over anhydrous sodium sulfate. Solvent removal at reduced pressure gave a pale yellow resin. Crystallization of this material from ether gave two crops of racemic 7-(3,5-dimethyl-4 -isoxazolyl)-5-oxo-heptanoic acid as a fine white powder, m.p. 61.5°-63,5°.

後処理

  1. customto destroy the excess oxidizing agent
  2. custommost of the acetone was removed at reduced pressure
  3. additionThe residue was diluted with water, saturated with sodium chloride
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solutions were washed with brine
  6. washThe sodium bicarbonate solutions were washed with ether
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate solutions were washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customSolvent removal at reduced pressure
  11. customgave a pale yellow resin
  12. customCrystallization of this material from ether

出典と根拠

ORDレコード
ord-27c3aae9c1ba46de9b140bed2f2f25ec
出典データセット
uspto-grants-1977_08
特許番号
US04044004

関連ノート

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