Acetic Acid → 3-Acetyl-3-phenylfuran

HRID 486555ノート

反応式

HRID 486555 の反応式
[C:1]1([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](O)(=[O:14])[CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)C>[C:12]([C:10]1[O:9][CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1)(=[O:14])[CH3:13].[C:12]([C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=[CH:10][O:9][CH2:8]1)(=[O:14])[CH3:13]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 5188023-Phenylfuran

生成物 2

HCID 190953503-Acetyl-3-phenylfuran収率 43%HCID 190954162-Acetyl-4-phenylfuran収率 13%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

3-Phenylfuran (4.3 g) was dissolved in 80 ml of acetonitrile under argon and treated while stirring with 8.6 g of the mixed anhydride from acetic acid and p-toluenesulphonic acid. The reaction solution was stirred at room temperature for 64 hours and subsequently stirred with 150 ml of saturated sodium hydrogen carbonate solution and 150 ml of diethyl ether 30 minutes. The phases were separated and the aqueous phase was extracted once with a further 100 ml of diethyl ether. The organic phases were combined, washed with 100 ml of water, dried over MgSO4 and freed from solvent. The residue was chromatographed on 200 g of silica gel with methylene chloride/hexane (1:1) as the eluent. There was obtained 0.7 g (13%) of 2-acetyl-4-phenylfuran besides 2.4 g (43%) of 3-acetyl-3-phenylfuran. The former was processed without further purification.

後処理

  1. additiontreated
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted once with a further 100 ml of diethyl ether
  4. washwashed with 100 ml of water
  5. dry with materialdried over MgSO4
  6. customThe residue was chromatographed on 200 g of silica gel with methylene chloride/hexane (1:1) as the eluent

出典と根拠

ORDレコード
ord-8ef7e02077ef485fa784be232c746b00
出典データセット
uspto-grants-1994_03
特許番号
US05292732

反応ノート

読み込み中…