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

HRID 982060ノート

反応式

HRID 982060 の反応式
[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

参加物

6

反応物 4

HCID 3283Diethyl Ether3 回HCID 2724682Lithium diisopropylamideHCID 10964544N-cyclohexylethanimineHCID 146775263-(4-Fluorophenyl)bicyclo[3.2.1]oct-2-ene-2-carboxaldehyde

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ddfcf004e18c4ab9bf9130556ca15ff7
出典データセット
uspto-grants-1991_02
特許番号
US04994494

反応ノート

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