2-Chloroanisole → 1-Benzyl-3-(3-methoxyphenyl)-2-azepanone

HRID 848414ノート

反応式

HRID 848414 の反応式
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)CCCC(C)(C)N1.C([Li])CCC.Cl[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39]>O1CCCC1.CCCCCC.O>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([O:38][CH3:39])[CH:32]=2)[C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 130112-ChloroanisoleHCID 130352,2,6,6-TetramethylpiperidineHCID 14910681-Benzylazepan-2-oneHCID 178418339Butyllithium2 回

生成物 1

HCID 205653371-Benzyl-3-(3-methoxyphenyl)-2-azepanone

試薬・触媒・溶媒 3

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

反応条件

温度
0 °C

実験手順

1-Benzylhexahydro-2H-azepin-2-one (10.2 g) in tetrahydrofuran (100 ml) was added dropwise to a stirred, cooled solution of lithium-2,2,6,6-tetramethylpiperidide [prepared by the addition of 2,2,6,6-tetramethylpiperidine (8.5 g) to butyl lithium (0.05 mole) in hexane (32 ml)] under nitrogen. When the addition was completed a further portion of butyl lithium (0.05 mole) in hexane (32 ml) was added. The solution was cooled to 0° C. and o-chloroanisole (6.2 ml) added dropwise. After stirring at room temperature for four hours the reaction was decomposed with water and the solvents removed under reduced pressure. The resulting oil was partitioned between 5 M hydrochloric acid and toluene. After drying (MgSO4) the toluene was removed to leave an oil which was distilled affording 5.02 g b.p. 180°-220° C. at 0.2 mm. The oil was crystallised from methanol, affording 3.15 g m.p. 120°-122° C.

後処理

  1. additionWhen the addition
  2. additionwas added
  3. customthe solvents removed under reduced pressure
  4. customThe resulting oil was partitioned between 5 M hydrochloric acid and toluene
  5. dry with materialAfter drying (MgSO4) the toluene
  6. customwas removed
  7. customto leave an oil which
  8. distillationwas distilled
  9. customaffording 5.02 g b.p. 180°-220° C. at 0.2 mm
  10. customThe oil was crystallised from methanol
  11. customaffording 3.15 g m.p. 120°-122° C.

出典と根拠

ORDレコード
ord-1431711e01d04526923d1330c5bbef03
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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