4-Iodophenol → 2-(2-(4-Iodophenoxy)ethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

HRID 710351ノート

反応式

HRID 710351 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][C:12]1[CH:13]2[CH2:18][CH:15]([CH2:16][CH:17]=1)[C:14]2([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][C:12]2[CH:13]3[CH2:18][CH:15]([CH2:16][CH:17]=2)[C:14]3([CH3:19])[CH3:20])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 202771482-(2-Bromoethyl)-6,6-dimethylbicyclo(3.1.1)hept-2-ene2 回

生成物 1

HCID 667267162-(2-(4-Iodophenoxy)ethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene収率 28.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4-iodophenol (0.4 g; 1.82 mmol), 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene (0.45 g, 1.97 mmol) and K2CO3 (0.3 g, 2.17 mmol) in anhydrous DMF (5 ml) was stirred overnight at room temperature. Another portion of 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene (0.3 g) was added and stirring was continued for 6 h. The mixture was diluted to 50 ml with EtOAc and washed with H2O (50 ml). The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) to give the title product (0.189 g; 28%), as pale paste. 1H-NMR (CDCl3) 0.81 (s, 3H); 1.26 (s, 3H); 2.06-2.44 (m, 8H); 3.91 (tr, 2H, J=6.97 Hz); 5.32 (s, 1H); 6.64 (d, 2H, J=8.96 Hz); 7.51 (d, 2H, J=8.96 Hz).

後処理

  1. stirringstirring
  2. waitwas continued for 6 h
  3. washwashed with H2O (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by FCC (SiO2)

出典と根拠

ORDレコード
ord-98d837e8d00a431dbda479b6a2edd2d8
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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