Water → HCID 70270704, compound

HRID 2289378Notes

Reaction equation

HRID 2289378 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][C@@H:14]([C@@H:20]([CH3:23])[CH2:21][CH3:22])[C:15](OCC)=[O:16].O.[OH-].[Na+]>C1COCC1>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][C@@H:14]([C@@H:20]([CH3:23])[CH2:21][CH3:22])[CH2:15][OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57144221HCID 57144221, compound

Product 1

HCID 70270704HCID 70270704, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In a 50 ml flask were charged 1.2 g of lithium aluminum hydride and 50 ml of THF, and a solution of 7.85 g of the compound obtained in Step 2 in 20 ml of THF was added thereto dropwise under ice-cooling, followed by stirring at room temperature for 1 hour. Then, 1.2 ml of water and 20 ml of THF were added thereto dropwise over 15 minutes. To the reaction mixture was further added dropwise 3.6 ml of a 4% sodium hydroxide aqueous solution under cooling with ice over 40 minutes, followed by filtration through zeolite. The filtrate was distilled under reduced pressure to remove the solvent, and the resulting crude product was purified by silica gel column chromatography to obtain 5.9 g (20.9%) of the titled compound.

Workup

  1. temperaturedropwise under ice-cooling
  2. waitdropwise over 15 minutes
  3. temperatureunder cooling with ice over 40 minutes
  4. filtrationfollowed by filtration through zeolite
  5. distillationThe filtrate was distilled under reduced pressure
  6. customto remove the solvent
  7. customthe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3cac3625d08c401982e9aa1ca5cd989e
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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