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

HRID 848414노트

반응식

HRID 848414 반응식
[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

참가 물질

8

반응물 4

HCID 130112-ChloroanisoleHCID 130352,2,6,6-TetramethylpiperidineHCID 14910681-Benzylazepan-2-oneHCID 178418339Butyllithium2회

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-1431711e01d04526923d1330c5bbef03
출처 데이터셋
uspto-grants-1981_10
특허 번호
US04296029

반응 노트

불러오는 중…