Dimethylformamide → HCID 68002053、化合物

HRID 717647ノート

反応式

HRID 717647 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].CN(C=O)C.Br[CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][CH:22]2[CH2:25][CH:20]1[C:21]2([CH3:27])[CH3:26]>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH:22]3[CH2:25][CH:20]2[C:21]3([CH3:26])[CH3:27])=[CH:4][CH:3]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 108944-IodophenolHCID 24758Sodium hydrideHCID 190944812-(2-Bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane

生成物 1

HCID 68002053HCID 68002053、化合物収率 190.4%

実験手順

To a stirred suspension of 4-iodophenol (0.5 g; 2.27 mmol) and 60% NaH (0.16 g, 2.3 mmol) in anhydrous DMF (5 ml) 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane (0.5 g, 2.2 mmol) was added the and mixture was stirred for 3 h at room temperature. After addition of more of 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane (0.2 g) the mixture was stirred for additional 2 h, quenched with NH4Cl solution and diluted to 20 ml with EtOAc. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.61 g, 73%), as a colourless paste. 1H-NMR (CDCl3) 7.51 (d, 2H, J=8.91 Hz); 6.64 (d, 2H, J=8.88 Hz); 3.88 (t, 2H, J=3.21 Hz); 2.34-1.84 (m, 10H); 1.17 (s, 3H); 1.01 (s, 3H).

後処理

  1. additionwas added the and mixture
  2. stirringwas stirred for additional 2 h
  3. customquenched with NH4Cl solution
  4. additiondiluted to 20 ml with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by FCC (SiO2, hexane/EtOAc)

出典と根拠

ORDレコード
ord-1598983820a5444ca432cfc2b84381d2
出典データセット
uspto-grants-2015_11
特許番号
US09193716B2

反応ノート

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