Water → HCID 59714981, compound

HRID 2223865Notes

Reaction equation

HRID 2223865 reaction equation
C(OC(C(CC(O)=O)C(O)=O)=O)C.C([C:16](CC)([OH:51])[C:17]([CH2:23][CH2:24][C:25]1([CH2:31][CH2:32][O:33][Si:34]([C:47]([CH3:50])([CH3:49])[CH3:48])([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)([CH2:21][OH:22])[CH2:18][CH2:19][OH:20])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[O:33]([CH2:32][CH2:31][C:25]1([CH2:24][CH2:23][C:17]([CH2:21][OH:22])([CH2:18][CH2:19][OH:20])[CH2:16][OH:51])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[Si:34]([C:47]([CH3:49])([CH3:50])[CH3:48])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131726888HCID 131726888, compound

Product 1

HCID 59714981HCID 59714981, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of diethyl 2-[2-[1-[2-(tert-Butlydiphenylsiloxy)ethyl]cyclohexyl]ethyl]-2-hydroxymethylbutane-1,4-diol ethoxycarbonylsuccinate (1.0 g) in diethyl ether (20 mL) was added lithium aluminum hydride (178 mg) under ice cooling. After stirring the solution under ice cooling for 1.5 hours, water (0.18 mL) and a 15% aqueous sodium hydroxide solution (0.18 mL) were successively added thereto. The solution was stirred at room temperature for 15 minutes. Water (0.54 mL) was then added to the solution, and it was stirred at room temperature for additional 30 minutes. The solution was dried over anhydrous magnesium sulfate and filtered. Chloroform was added to the solid, and the solution was stirred at room temperature for 2 hours, followed by filtration. The combined filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:4) to give the title compound (230 mg)

Workup

  1. stirringThe solution was stirred at room temperature for 15 minutes
  2. stirringwas stirred at room temperature for additional 30 minutes
  3. dry with materialThe solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. additionChloroform was added to the solid
  6. stirringthe solution was stirred at room temperature for 2 hours
  7. filtrationfollowed by filtration
  8. concentrationThe combined filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-2f5868efa257437ba594860214a35f5f
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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