Water → 2-[(2-Bromophenyl)methyl]-6-[(phenylmethoxy)methyl]-cyclohexanone

HRID 1460606노트

반응식

HRID 1460606 반응식
[C:1]1([CH2:7][O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCCC1.[Br:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br.O>C1C=CC=CC=1>[Br:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][CH:12]1[CH2:13][CH2:14][CH2:15][CH:10]([CH2:9][O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]1=[O:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 31268PyrrolidineHCID 769652-Bromobenzyl bromideHCID 10489011Cyclohexanone, 2-[(phenylmethoxy)methyl]-

생성물 1

HCID 198011362-[(2-Bromophenyl)methyl]-6-[(phenylmethoxy)methyl]-cyclohexanone

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a solution of the ketone of Example 113 in benzene is added pyrrolidine (4 equivalents). The mixture is heated to reflux for 24 hours removing the water formed by use of a Dean-Stark type apparatus. The reaction mixture is concentrated in vacuo. The organics are dissolved in dioxane followed by addition of 2-bromobenzyl bromide (1.5 equivalents). The mixture is heated to reflux for 6 hours. Water is added and the refluxing continued for 3 hours. The solution is concentrated in vacuo to dryness. The remaining organics are partitioned between ether and water. The ether layer is dried (MgSO4), concentrated in vacuo, then chromatographed to give the title compound.

후처리

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 hours
  3. customremoving the water
  4. customformed by use of a Dean-Stark type apparatus
  5. concentrationThe reaction mixture is concentrated in vacuo
  6. dissolutionThe organics are dissolved in dioxane
  7. temperatureThe mixture is heated
  8. temperatureto reflux for 6 hours
  9. concentrationThe solution is concentrated in vacuo to dryness
  10. customThe remaining organics are partitioned between ether and water
  11. dry with materialThe ether layer is dried (MgSO4)
  12. concentrationconcentrated in vacuo
  13. customchromatographed

출처 및 근거

ORD 기록
ord-eb81b68a4b3247419ef4cd02f179247a
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05071853

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