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

HRID 2395817Notes

Reaction equation

HRID 2395817 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aa808d24c4684d70a68d352b92a2b058
Source dataset
uspto-grants-1996_02
Patent number
US05489613

Reaction notes

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