Diethyl Malonate → Diethyl tetrahydropyran-4,4-dicarboxylate

HRID 49040

反応式

HRID 49040 の反応式
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br>C(O)C>[O:19]1[CH2:20][CH2:21][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])([C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH2:17][CH2:18]1

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 21521Bis(2-bromoethyl) etherHCID 2723922Sodium ethoxide

生成物 1

HCID 239606Diethyl tetrahydropyran-4,4-dicarboxylate収率 61.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Diethyl malonate (32.0 g) was added to a solution of sodium ethoxide (1 equivalent) in ethanol and the solution was stirred for 30 min. 2-Bromoethyl ether (46.0 g) was then added and the mixture was stirred at reflux for 3 h. The mixture was then cooled, evaporated in vacuo and the residue partitioned between water and dichloromethane. The organic layer was separated and washed with water and brine, then dried (MgSO4) and evaporated. The residue was then purified by flash column chromatography on silica gel, eluting with 4:1 hexanes/ether, to give the title compound (28.0 g) as colourless liquid.

後処理

  1. stirringthe mixture was stirred
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was then cooled
  4. customevaporated in vacuo
  5. customthe residue partitioned between water and dichloromethane
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was then purified by flash column chromatography on silica gel
  11. washeluting with 4:1 hexanes/ether

出典と根拠

ORDレコード
ord-eedaf22714fd417fb04112ffc63e919e
出典データセット
uspto-grants-2004_03
特許番号
US06706719B1

関連ノート

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