Diethyl Ether → 3-[3-(4-Fluorophenyl)bicyclo[3.2.1]oct-2-en-2-yl]-propenal

HRID 982060노트

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HRID 982060 반응식
[Li+].CC([N-]C(C)C)C.C(=NC1CCCCC1)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:31][CH:30]3[CH2:32][CH:27]([CH2:28][CH2:29]3)[C:26]=2[CH:33]=O)=[CH:21][CH:20]=1.CC[O:37][CH2:38][CH3:39]>O>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH2:31][CH:30]3[CH2:32][CH:27]([CH2:28][CH2:29]3)[C:26]=2[CH:33]=[CH:39][CH:38]=[O:37])=[CH:23][CH:24]=1

참가 물질

6

반응물 4

HCID 3283Diethyl Ether3회HCID 2724682Lithium diisopropylamideHCID 10964544N-cyclohexylethanimineHCID 146775263-(4-Fluorophenyl)bicyclo[3.2.1]oct-2-ene-2-carboxaldehyde

생성물 1

HCID 537275483-[3-(4-Fluorophenyl)bicyclo[3.2.1]oct-2-en-2-yl]-propenal

시약·촉매·용매 1

HCID 962Water용매

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온도
-70 °C

실험 절차

To a 0°-5° C. solution of LDA (26.5 mmoles) in 25 ml anhydrous ether was added ethylidenecyclohexylamine (Org. Syn. 50 66) (3.32 g, 26.5 mmoles) in 25 ml anhydrous ether. The solution was stirred for 10 minutes, cooled to -70° C. and 3-(4-fluorophenyl)bicyclo[3.2.1]oct-2-ene-2-carboxaldehyde (5.55 g, 24.1 mmoles) in 25 ml ether was added. The solution was stirred for 60 minutes, warmed to 0°-5° C., stirred for 90 minutes and diluted with water. The organic layer was washed with water and brine and dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was purified by HPLC using 3% ethyl acetate in hexanes as the eluent. Concentration in vacuo of the product rich fractions provided 2.53 g of the product as an orange oil.

후처리

  1. stirringThe solution was stirred for 60 minutes
  2. temperaturewarmed to 0°-5° C.
  3. stirringstirred for 90 minutes
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customRemoval of the volatiles in vacuo
  7. customprovided a residue which
  8. customwas purified by HPLC
  9. concentrationConcentration in vacuo of the product rich fractions

출처 및 근거

ORD 기록
ord-ddfcf004e18c4ab9bf9130556ca15ff7
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994494

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