Potassium Carbonate → 1-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-propan-1-one

HRID 1671352

反応式

HRID 1671352 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:13])[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][O:23][CH3:24]>CN(C=O)C>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([C:10](=[O:13])[CH2:11][CH3:12])=[C:2]([O:1][CH2:21][CH2:22][O:23][CH3:24])[CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 2348362'-Hydroxy-4'-methoxypropiophenone

生成物 1

HCID 673372111-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-propan-1-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1-(2-hydroxy-4-methoxyphenyl)propan-1-one (1 g, 5.55 mmol) in DMF (50 ml) is treated with potassium carbonate (0.920 g, 6.66 mmol) and stirred at RT for approximately 10 mins. 1-Bromo-2-methoxyethane (0.771 g, 5.55 mmol) is added and the mixture is stirred at RT overnight. The solvent is removed in vacuo and the residue is partitioned between in EtOAc/H2O. The organic phase is separated and washed with sat Na2CO3, 1M HCl, brine, dried (MgSO4) and concentrated in vacuo to afford a dark green/brown oil. Purification by chromatography on silica gel (50 g+70 g) eluting with 20% EtOAc/iso-hexane affords the title compound; MS m/z 239.2 [M+H]+.

後処理

  1. stirringthe mixture is stirred at RT overnight
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between in EtOAc/H2O
  4. customThe organic phase is separated
  5. washwashed with sat Na2CO3, 1M HCl, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto afford a dark green/brown oil
  9. customPurification by chromatography on silica gel (50 g+70 g)
  10. washeluting with 20% EtOAc/iso-hexane

出典と根拠

ORDレコード
ord-5a16cbcca7664ac1b88171ef6a04dd0c
出典データセット
uspto-grants-2011_08
特許番号
US07994203B2

関連ノート

読み込み中…