2-Chloroanisole → 3-Ethylhexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

HRID 848412ノート

反応式

HRID 848412 の反応式
CC1(C)CCCC(C)(C)N1.C([Li])CCC.[CH2:16]([CH:18]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([CH3:25])[C:19]1=[O:26])[CH3:17].Cl[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35]>CCCCCC.O1CCCC1.O>[CH2:16]([C:18]1([C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([O:34][CH3:35])[CH:28]=2)[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([CH3:25])[C:19]1=[O:26])[CH3:17]

参加物

8

反応物 4

HCID 130112-ChloroanisoleHCID 130352,2,6,6-TetramethylpiperidineHCID 1084053-Ethylhexahydro-1-methyl-2H-azepin-2-oneHCID 178418339Butyllithium2 回

生成物 1

HCID 27290973-Ethylhexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒2 回

実験手順

2,2,6,6-tetramethylpiperidine (8.48 g) was added dropwise with cooling and stirring under nitrogen to a solution of butyl lithium (0.05 mole) in hexane (31.25 ml) and tetrahydrofuran (15 ml). 3-Ethylhexahydro-1-methyl-2H-azepin-2-one (7.75 g) in dry tetrahydrofuran (20 ml) was added. On completion of this addition a further portion of butyl lithium (0.06 mole) in hexane (37.5 ml) was added with cooling. After ten minutes o-chloroanisole (8.54 g) was added dropwise in tetrahydrofuran (20 ml). The reaction was then stirred at ambient temperature for c.a. 20 hours. The reaction mixture was poured into water, and the tetrahydrofuran removed under reduced pressure. After acidifying with 5 M hydrochloric acid the mixture was extracted with toluene. Toluene extracts were washed with water, dried (MgSO4) and after removal of the solvent the product distilled affording 2.37 g, b.p. 150°-170° C. at 0.6 mm. Corrected by purity by g.l.c. assay, the yield of the title compound was 15.8%.

後処理

  1. temperaturewith cooling
  2. additionwas added
  3. temperaturewith cooling
  4. custom20 hours
  5. customthe tetrahydrofuran removed under reduced pressure
  6. extractionwas extracted with toluene
  7. washToluene extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customafter removal of the solvent the product
  10. distillationdistilled
  11. customaffording 2.37 g, b.p. 150°-170° C. at 0.6 mm

出典と根拠

ORDレコード
ord-b4fe3d5fa45245a9ba6d5b2e3713cd90
出典データセット
uspto-grants-1981_10
特許番号
US04296029

反応ノート

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