Diethyl Ether → HCID 59714891, compound

HRID 2223861Notes

Reaction equation

HRID 2223861 reaction equation
C[O:2][C:3]([CH2:5][C:6]1([CH:12]([C:17](OC)=[O:18])[C:13](OC)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[OH-].[Na+]>O1CCCC1.O>[OH:2][CH2:3][CH2:5][C:6]1([CH:12]([CH2:13][OH:14])[CH2:17][OH:18])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23021238HCID 23021238, compound

Product 1

HCID 59714891HCID 59714891, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 2-(1-methoxycarbonylmethylcyclohexyl)malonate (490 mg) in tetrahydrofuran (15 mL) was added lithium aluminum hydride (195 mg) under ice cooling. The solution was stirred under reflux for 1 hour, and then, cooled on ice. Diethyl ether was added to the solution, followed by addition of water (0.2 mL) and a 15% aqueous sodium hydroxide solution (0.2 mL). After stirring the solution at room temperature for 15 minutes, water (0.6 mL) was added thereto, and it was stirred at room temperature for additional 30 minutes. The solution was dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, chloroform:methanol=85:15) to give the title compound (200 mg).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled on ice
  3. stirringAfter stirring the solution at room temperature for 15 minutes
  4. stirringit was stirred at room temperature for additional 30 minutes
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography (silica gel, chloroform:methanol=85:15)

Sources & evidence

ORD record
ord-ea16bcf536c8479386d2886ba2fbb5ae
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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