Water → HCID 59714946, compound

HRID 2223859Notes

Reaction equation

HRID 2223859 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1([CH2:17][CH2:18][CH:19]([C:24](OC)=[O:25])[C:20](OC)=[O:21])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1([CH2:17][CH2:18][CH:19]([CH2:20][OH:21])[CH2:24][OH:25])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59714843HCID 59714843, compound

Product 1

HCID 59714946HCID 59714946, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of dimethyl 2-[2-[1-(2-benzyloxyethyl)-cyclohexyl]ethyl]malonate (1.03 g) in diethyl ether (40 mL) was added lithium aluminum hydride (207 mg) under ice cooling. After stirring the solution under ice cooling for 2 hours, water (0.2 mL) and a 15% aqueous sodium hydroxide solution (0.2 mL) were successively added to the solution. The solution was stirred at room temperature for 15 minutes, water (0.6 mL) was added thereto, and it was stirred for additional 30 minutes. The solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=2:3) to give the title compound (320 mg)

Workup

  1. stirringThe solution was stirred at room temperature for 15 minutes
  2. stirringit was stirred for additional 30 minutes
  3. dry with materialThe solution was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-79fd71f3f2eb41b9ac1cd04c5b2812a8
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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