Water → HCID 15380894, compound

HRID 581064Notes

Reaction equation

HRID 581064 reaction equation
C[O:2][C:3]([C:5]1[C:14]2[O:13][CH:12]=[CH:11][O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[OH:2][CH2:3][C:5]1[C:14]2[O:13][CH:12]=[CH:11][O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15380893HCID 15380893, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15380894HCID 15380894, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.62 g (8.44 mmol) of the unsaturated ester obtained in Step C are added to a suspension of 0.64 g (16.84 mmol) of lithium aluminium hydride in 40 ml of anhydrous ether. The mixture is then heated at reflux for 30 minutes under an inert atmosphere and subsequently allowed to cool. The solution is hydrolysed with, in succession, 0.64 ml of water, 0.64 ml of a 15% sodium hydroxide solution and finally 1.92 ml of water. After 30 minutes' stirring, the salts are filtered off and then the filtrate is concentrated under reduced pressure. The title alcohol is obtained pure in the form of a white solid after chromatography over silica gel (eluant:AcOEt/PE:40/60).

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 30 minutes under an inert atmosphere
  3. temperatureto cool
  4. filtrationthe salts are filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-855fa76534cf4558bbc51a0b5a085a73
Source dataset
uspto-grants-1999_07
Patent number
US05919814

Reaction notes

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