Sodium Chloride → 5-[4-(4-Chlorophenyl)-1,3-butadienyl]-2,2-dimethyl-3(2H)-furanone

HRID 359362ノート

反応式

HRID 359362 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH:8]=O)=[CH:4][CH:3]=1.[CH3:12][C:13]1([CH3:20])[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[O:14]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH:8]=[CH:19][C:15]2[O:14][C:13]([CH3:20])([CH3:12])[C:17](=[O:18])[CH:16]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-HCID 3794977p-Chlorocinnamaldehyde

生成物 1

HCID 542263425-[4-(4-Chlorophenyl)-1,3-butadienyl]-2,2-dimethyl-3(2H)-furanone収率 42.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of p-chlorocinnamaldehyde (2.7 g, 16.2 mM) and 2,2,5-trimethyl-3(2H)-furanone (2.45 g, 19.4 mM) in ethanol (100 mL), was added 1N aqueous sodium hydroxide (32 mL, 3.2 mM). The reaction solution was stirred at room temperature for one day. After saturated aqueous sodium chloride (400 mL) was added, the aqueous layer was extracted with diethyl ether (3×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a brown solid. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to afford yellow crystals (1.9 g, 36% yield), m.p. 95°-96° C.

後処理

  1. extractionthe aqueous layer was extracted with diethyl ether (3×100 mL)
  2. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown solid
  7. customThe crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)

出典と根拠

ORDレコード
ord-775556e7942c468a8e4813c7d972b8c0
出典データセット
uspto-grants-1991_03
特許番号
US05001126

反応ノート

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