Water → 1-Allyl-7-methoxy-2-tetralone

HRID 26392

반응식

HRID 26392 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1.N1C[CH2:17][CH2:16][CH2:15]1.O.C(Br)C=C>C1C=CC=CC=1>[CH2:17]([CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:13])[CH:16]=[CH2:15]

참가 물질

6

반응물 4

HCID 962Water2회HCID 7841Allyl bromideHCID 31268PyrrolidineHCID 777857-Methoxy-2-tetralone

생성물 1

HCID 233308001-Allyl-7-methoxy-2-tetralone

시약·촉매·용매 1

HCID 241Benzene용매3회

실험 절차

To a solution of 104.1 g (0.59 mole) 3,4-dihydro-7-methoxy-2(1H)naphthalenone in 100 ml dry benzene was added dropwise under nitrogen with stirring at room temperature 62.5 g (0.88 mole) pyrrolidine. After the addition (10-15 min), the reaction mixture was refluxed for 2.5 hr with azeotropic removal of water and then cooled to room temperature. The enamine solution was added dropwise to 143.8 g (1.19 mole) allyl bromide with stirring at a rate sufficient to maintain normal refluxing to provide a heavy precipitate. Benzene (50 ml) was added to facilitate stirring and reflux continued for 4 hr; then, 700 ml of water was added and refluxing resumed. After 2 hr, the reaction mixture was cooled to room temperature and diluted with 100 ml benzene. The benzene layer was separated and the aqueous phase extracted with benzene (2×100 ml). The combined extracts were washed with water (2×100 ml) and dried (Na2SO4). After evaporation of the solvent, the residue was distilled to give 113.5 g (89%) of VIIIa, b.p. 114°-118°/0.1-0.05 mm Hg. NMR: δ 2.40-3.10 (m, 6, allylic and alicyclic), 3.45 (t, 1, C1 --H, J=6.5), 3.75 (s, 3, OCH3), 4.8-6.1 (m, 3, olefinic), 6.7-7.2 (m, 3, ArH). IR: (neat) 1715 cm-1.

후처리

  1. additionAfter the addition (10-15 min)
  2. temperatureto maintain normal
  3. temperaturerefluxing
  4. customto provide a heavy precipitate
  5. stirringto facilitate stirring
  6. temperaturereflux
  7. temperaturerefluxing
  8. waitAfter 2 hr
  9. temperaturethe reaction mixture was cooled to room temperature
  10. customThe benzene layer was separated
  11. extractionthe aqueous phase extracted with benzene (2×100 ml)
  12. washThe combined extracts were washed with water (2×100 ml)
  13. dry with materialdried (Na2SO4)
  14. customAfter evaporation of the solvent
  15. distillationthe residue was distilled
  16. customto give 113.5 g (89%) of VIIIa, b.p. 114°-118°/0.1-0.05 mm Hg

출처 및 근거

ORD 기록
ord-0b01ddd67fd5443fba10aef5a19ba100
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04150032

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