Water → HCID 68421468, compound

HRID 1881345Notes

Reaction equation

HRID 1881345 reaction equation
[CH:1](=[C:8]([C:10]([CH2:15][OH:16])([CH2:13][OH:14])[CH2:11][OH:12])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([C:19](CC)([C:23](O)=[O:24])[C:20](O)=[O:21])C.C([C:30](CC)([C:34](O)=[O:35])[C:31](O)=[O:32])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH:1](=[C:8]([C:10]([CH2:11][OH:12])([CH2:13][OH:14])[CH2:15][OH:16])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([OH:24])[CH2:19][CH2:20][OH:21].[CH2:34]([OH:35])[CH2:30][CH2:31][OH:32]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68421069HCID 68421069, compound

Product 1

HCID 68421468HCID 68421468, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

Bis-(diethyl malonate) monobenzalpentaerythritol (100 mmol) dissolved in diethyl ether (100 mL) is added dropwise to a lithium aluminium hydride in diethyl ether (100 mL) suspension. The mixture is stirred for 2 h at reflux temperature and 20 h at 20° C. After cooling at 5° C., water (5 mL), 2 N aqueous solution of sodium hydroxide (10 mL) and water (5 mL) is successively added. The suspension is filtered, the solid is washed with diethylether and the combined filtrates are dried (Na2SO4) and concentrated under vacuum. The crude product is chromatographed on silica gel using a solvent ethyl acetate as eluent to give the product.

Workup

  1. temperatureAfter cooling at 5° C.
  2. filtrationThe suspension is filtered
  3. washthe solid is washed with diethylether
  4. dry with materialthe combined filtrates are dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customThe crude product is chromatographed on silica gel using a solvent ethyl acetate as eluent
  7. customto give the product

Sources & evidence

ORD record
ord-3d410a5ad0ab4d3ea6196abcc613c6d9
Source dataset
uspto-grants-2012_11
Patent number
US08318795B2

Reaction notes

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