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

HRID 2165423ノート

反応式

HRID 2165423 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4b806522799a4ad197a47354514c462d
出典データセット
uspto-grants-1990_07
特許番号
US04939267

反応ノート

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