Water → HCID 59714835, compound

HRID 2223841Notes

Reaction equation

HRID 2223841 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][O:3][C:2]1=[O:12].[H-].C([Al+]CC(C)C)C(C)C.O.[OH-].[Na+]>C(OCC)C>[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][O:3][CH:2]1[OH:12]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 224123-Oxaspiro(5,5)undecan-2-oneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 59714835HCID 59714835, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a solution of 3-oxaspiro[5.5]undecan-2-one (1.68 g) in diethyl ether (50 mL) was added a 1M solution of diisobutylaluminum hydride in diethyl ether (15.0 mL) under ice cooling. The solution was stirred under ice cooling for 15 minutes. Diethyl ether (100 mL) was then added to the solution, followed by successive addition of water (0.6 mL) and a 15% aqueous sodium hydroxide solution (0.6 mL). The solution was stirred at room temperature for 30 minutes. Water (1.8 mL) was then added to the solution, and it was stirred for additional 15 minutes. The solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=1:1) to give the title compound (1.36 g).

Workup

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

Sources & evidence

ORD record
ord-7e48a54e08d74841be9839c1be46ecf7
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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