Sodium Hydroxide → 3-(5-Hydroxypentylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane

HRID 2395817ノート

反応式

HRID 2395817 の反応式
[C:1]([CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:15][C@@H:14]2[C@@H:10]([CH2:11][C:12]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:13]2)[CH2:9]1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[OH:2][CH2:1][CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:15][C@@H:14]2[C@@H:10]([CH2:11][C:12]3([O:16][CH2:17][CH2:18][O:19]3)[CH2:13]2)[CH2:9]1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 228526373-(4-Carboxybutylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane

生成物 1

HCID 228526963-(5-Hydroxypentylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane収率 100.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

49.10 g of 3-(4-carboxybutylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane (prepared as described in Preparation 1) in 150 ml of tetrahydrofuran were added dropwise to a suspension of 10.50 g of lithium aluminum hydride in 675 ml of tetrahydrofuran, whilst cooling with ice. The mixture was then heated under reflux for 80 minutes. Upon completion of the reaction, 42 ml of a 4% w/v aqueous solution of sodium hydroxide were added, and the mixture was stirred at room temperature. The resulting precipitate was removed by filtration, and the filtrate was condensed by evaporation under reduced pressure, giving 46.90 g of a residue. On purifying the residue by silica gel column chromatography, 40.10 g of the title compound were obtained as an oil, from the fractions eluted with hexane containing 20-30% by volume of ethyl acetate.

後処理

  1. temperaturewhilst cooling with ice
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for 80 minutes
  4. additionwere added
  5. customThe resulting precipitate was removed by filtration
  6. customcondensed
  7. customby evaporation under reduced pressure

出典と根拠

ORDレコード
ord-aa808d24c4684d70a68d352b92a2b058
出典データセット
uspto-grants-1996_02
特許番号
US05489613

反応ノート

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