Dimethylamine → 4-Dimethylamino-1-phenyl-3-butene-2-one

HRID 1584637ノート

反応式

HRID 1584637 の反応式
[CH3:1][N:2]([CH3:13])[CH2:3][C:4]#[C:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(CC#C)C=CC=CC=1.C=O.CNC.ClC1C=C(C=CC=1)C(OO)=[O:33]>ClCCl>[CH3:13][N:2]([CH3:1])[CH:3]=[CH:4][C:5](=[O:33])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

7

反応物 5

HCID 674DimethylamineHCID 712FormaldehydeHCID 70297m-Chloroperbenzoic acidHCID 575753BenzylacetyleneHCID 21225058HCID 21225058、化合物

生成物 1

HCID 545705994-Dimethylamino-1-phenyl-3-butene-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To an ice cold solution of 1-dimethylamino-4-phenyl-2-butyne (0.5 g; prepared by the Mannich reaction of 3-phenyl-1-propyne with formaldehyde and dimethylamine as per Mornet, et.al. Bull.Soc.Chim.Fr. 1974, 206) in dichloromethane (12 ml) was added in small portions 3-chloroperoxybenzoic acid (0.52 g). After the reaction was stirred at 0° C. for 20 minutes, the mixture was passed over twenty weight equivalents of basic alumina (Brockmann Grade I, 150 mesh) and the N-oxide was eluted using a solution of 10% methanol in dichloromethane. All fractions containing the desired amine N-oxide were combined and evaporated to near dryness in vacuo. The residue was treated successively three times with small portions of methanol (ca. 10 ml) followed by evaporation to near dryness, and the volume of the solution was adjusted to 25 mL by addition of methanol. The methanolic solution of the N-oxide was heated to reflux for approximately 4 hours and cooled. The solvent was evaporated to dryness in vacuo and the residue was chromatographed over silica gel (95:5 ethyl acetate-hexanes was used as the eluant) to give upon evaporation of the solvent in vacuo the desired product as an oil. MS(+ES) m/z: 190 (M+H)+.

後処理

  1. washthe N-oxide was eluted
  2. additionAll fractions containing the desired amine N-oxide
  3. customevaporated
  4. additionThe residue was treated successively three times with small portions of methanol (ca. 10 ml)
  5. customfollowed by evaporation
  6. additionthe volume of the solution was adjusted to 25 mL by addition of methanol
  7. temperatureThe methanolic solution of the N-oxide was heated
  8. temperatureto reflux for approximately 4 hours
  9. temperaturecooled
  10. customThe solvent was evaporated to dryness in vacuo
  11. customthe residue was chromatographed over silica gel (95:5 ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-9b00bcf764d74c88946d8334b6a9109c
出典データセット
uspto-grants-1999_08
特許番号
US05932745

反応ノート

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