Tetrahydrofuran → Ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate

HRID 31749

反応式

HRID 31749 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.C1COCC1.[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21]C([O-])=O.[K+].[Cl-].[Mg+2].[Cl-]>C(Cl)(=O)C(Cl)=O.CN(C=O)C.C(#N)C.C(N(CC)CC)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:10](=[O:12])[CH2:21][C:20]([O:26][CH2:27][CH3:28])=[O:25])=[CH:13][CH:14]=1

参加物

9

反応物 4

HCID 8028TetrahydrofuranHCID 3446434Potassium ethyl malonateHCID 51387914-(Fur-2-yl)benzoic acidHCID 5360315Magnesium Chloride

生成物 1

HCID 22142724Ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒2 回HCID 65578Oxalyl chloride溶媒2 回

実験手順

The acid from Step 1 was converted to the acid chloride by refluxing in a mixture of oxalyl chloride (1.3 ml), THF (20 ml) and several drops of DMF. Small portions of oxalyl chloride were added until the reaction was homogeneous. Reflux continued for 0.5 hours, then the solvent was removed in vacuo to give the crude acid chloride. Meanwhile, potassium ethyl malonate (2.7 g) was reacted with anhydrous magnesium chloride (1.9 g) and triethylamine (2.21 ml) in dry acetonitrile (50 ml) at room temperature for 3 hours. Triethylamine (1 ml) was added, followed by addition of a solution of the acid chloride in acetonitrile. The mixture was then stirred overnight at room temperature, then concentrated to dryness. The residue was partitioned between toluene and 10% aqueous HCl. The organic layer was washed with 10% HCl and water, dried and was then concentrated to give crude ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate as a solid.

後処理

  1. temperatureReflux
  2. customthe solvent was removed in vacuo
  3. customto give the crude acid chloride
  4. concentrationconcentrated to dryness
  5. customThe residue was partitioned between toluene and 10% aqueous HCl
  6. washThe organic layer was washed with 10% HCl and water
  7. customdried
  8. concentrationwas then concentrated

出典と根拠

ORDレコード
ord-825e1fd4f92d46999bb219a64ae09682
出典データセット
uspto-grants-2008_09
特許番号
US07425557B2

関連ノート

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