Sodium Hydroxide → HCID 22664982, compound

HRID 392591Notes

Reaction equation

HRID 392591 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH:8]([C:15]1([C:20](OCC)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+].[OH-].[Na+]>CCOCC>[OH:7][CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]1([CH2:20][OH:21])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 22664977HCID 22664977, compound

Product 1

HCID 22664982HCID 22664982, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Under a nitrogen stream, lithium aluminum hydride (0.38 g, 0.01 mol) was suspended in dehydrating ether (8 ml) and ethyl 1-(1-hydroxy-1-phenylmethyl)cyclopentanecarboxylate (2.46 g, 0.01 mol) as 8 ml of a dehydrating ether solution was added dropwise over 30 min while stirring the mixture at room temperature. After the completion of dropwise addition, the mixture was stirred for 30 min while gently refluxing, then 10% aqueous sodium hydrogen carbonate (1 ml) was slowly added dropwise under ice-cooling. Then 20% aqueous sodium hydroxide (2 ml) was added dropwise and the ether layer was taken by decantation. The residue was washed twice with ether (10 ml). The ether layer was combined and the mixture was dehydrated over anhydrous magnesium sulfate and concentrated. The residual solution (2.01 g) was purified by silica gel column chromatography (ethyl acetate/hexane=2/3) to give the title compound (1.8 g) as a colorless oil (yield 87%).

Workup

  1. additionwas added dropwise over 30 min
  2. additionAfter the completion of dropwise addition
  3. stirringthe mixture was stirred for 30 min
  4. temperaturewhile gently refluxing
  5. temperaturecooling
  6. washThe residue was washed twice with ether (10 ml)
  7. concentrationconcentrated
  8. customThe residual solution (2.01 g) was purified by silica gel column chromatography (ethyl acetate/hexane=2/3)

Sources & evidence

ORD record
ord-3ef85cece17b404f91298720e8b979d9
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

Loading…