Potassium Carbonate → 3-Methyl-5-{5-[4-(5-oxazolyl)phenoxy]pentyl}isoxazole

HRID 2165423노트

반응식

HRID 2165423 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].S([CH2:37][N+:38]#[C-:39])(C1C=CC(C)=CC=1)(=O)=O>CO>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]3[O:18][CH:39]=[N:38][CH:37]=3)=[CH:19][CH:20]=2)[O:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 64834254-[5-(3-Methyl-5-isoxazolyl)pentyloxy]benzaldehyde

생성물 1

HCID 200639913-Methyl-5-{5-[4-(5-oxazolyl)phenoxy]pentyl}isoxazole수율 48%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A suspension of 10.00 g of 4-[5-(3-methyl-5-isoxazolyl)pentyloxy]benzaldehyde, 10.0 g of potassium carbonate and 7.14 g of tosylmethyl isocyanide (4-CH3C6H4 -SO2CH2NC) in 90 ml of methanol was heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo, and the residue was extracted with methylene dichloride. The extract was washed with water, the product isolated and recrystallized from isopropyl acetate-hexane. Further purification by flash filtration through a silica gel pad, eluting with isopropyl acetate, and recrystallization from isopropyl acetate-hexane gave 5.43 g (48%) of 3-methyl-5-{5-[4-(5-oxazolyl)phenoxy]pentyl}isoxazole, yellow powder, m.p. 91°-93° C.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionthe residue was extracted with methylene dichloride
  5. washThe extract was washed with water
  6. customthe product isolated
  7. customrecrystallized from isopropyl acetate-hexane
  8. customFurther purification
  9. filtrationby flash filtration through a silica gel pad
  10. washeluting with isopropyl acetate, and recrystallization from isopropyl acetate-hexane

출처 및 근거

ORD 기록
ord-4b806522799a4ad197a47354514c462d
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04939267

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