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

HRID 1287366노트

반응식

HRID 1287366 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-dee4388ed3874c2186f2053ddb7c35e2
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03984428

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