Sodium Hydroxide → HCID 59714887, compound

HRID 2223924Notes

Reaction equation

HRID 2223924 reaction equation
[CH2:1]1[C:4]2([CH2:9][CH2:8][O:7][C:6](=[O:10])[CH2:5]2)[CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C.O1CCCC1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C.O>[CH2:3]1[C:4]2([CH2:9][CH2:8][O:7][CH:6]([OH:10])[CH2:5]2)[CH2:1][CH2:2]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 59714955HCID 59714955, compoundHCID 86597605diisobutylaluminium hydride THF

Product 1

HCID 59714887HCID 59714887, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 7-oxaspiro[3.5]nonan-6-one (0.67 g) in tetrahedrofuran (3 mL) cooled at −78° C. was added 1M diisobutylaluminum hydride/tetrahydrofuran (1.0 mL) dropwise over 5 minutes. The reaction solution was stirred at that temperature for 1.5 hours. Water (40 μL) was added to the reaction solution. After allowing the temperature to rise to room temperature, a 15% aqueous sodium hydroxide solution (40 μL) and water (120 μL) were successively added to the solution. After stirring the solution at room temperature for 10 minutes, diethyl ether (2 mL) and anhydrous magnesium sulfate (0.17 g) were added. The solution was stirred for additional 30 minutes. The reaction solution was then filtered with Celite. The filtrate was concentrated under reduced pressure to give the title compound (230 mg).

Workup

  1. customto rise to room temperature
  2. stirringAfter stirring the solution at room temperature for 10 minutes
  3. stirringThe solution was stirred for additional 30 minutes
  4. filtrationThe reaction solution was then filtered with Celite
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-98ca5bcc8d8a49c6b6530eb35777f98c
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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