Water → HCID 14157577, compound

HRID 1734242Notes

Reaction equation

HRID 1734242 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C@H:12]1[C@H:16]([C:17](OCC)=[O:18])[O:15][CH2:14][O:13]1)=O)C.O.[OH-].[Na+]>O1CCCC1>[OH:9][CH2:10][C@H:12]1[C@H:16]([CH2:17][OH:18])[O:15][CH2:14][O:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 6941513(4R,5R)-4,5-bis(ethoxycarbonyl)-1,3-dioxolaneHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 14157577HCID 14157577, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

300 ml of tetrahydrofuran was added dropwise to 43.61 g of lithium aluminum hydride while cooling with ice. To this was added dropwise a solution of 125.3 g of (4R,5R)-4,5-bis(ethoxycarbonyl)-1,3-dioxolane prepared in Example 13 in 200 ml of tetrahydrofuran and reacted while vigorously stirring under cooling with ice. After the addition, the mixture was reacted for one hour while refluxing. Then, water was added drop by drop to hydrolyze lithium aluminum hydride under cooling with ice. After the addition of 0.5 ml of 4 mol/l sodium hydroxide dropwise, the mixture was stirred for 30 minutes and filtered with suction. 700 ml of ethanol was added to the precipitate, and the mixture was heated at 60°-70° C., stirred, and filtered with suction. This procedure was repeated three times. All filtrates were combined and concentrated by evaporator to obtain a crude title compound.

Workup

  1. temperaturewhile cooling with ice
  2. customreacted
  3. temperatureunder cooling with ice
  4. additionAfter the addition
  5. customthe mixture was reacted for one hour
  6. temperaturewhile refluxing
  7. temperatureunder cooling with ice
  8. stirringthe mixture was stirred for 30 minutes
  9. filtrationfiltered with suction
  10. addition700 ml of ethanol was added to the precipitate
  11. temperaturethe mixture was heated at 60°-70° C.
  12. stirringstirred
  13. filtrationfiltered with suction
  14. concentrationconcentrated by evaporator

Sources & evidence

ORD record
ord-0df3e4f303024f14ab5e8512aa4d44dd
Source dataset
uspto-grants-1996_07
Patent number
US05532380

Reaction notes

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