1,4-Dioxaspiro[4.5]decan-8-one → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 2207793Notes

Reaction equation

HRID 2207793 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydride

Product 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-olYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.5]decan-8-one (244 g, 1.56 mol, 1.0 eq.) in MeOH (5 L) was slowly added NaBH4 (59 g, 1.56 mol, 1.0 eq.) keeping the internal temperature <10° C. using an ice bath. The ice bath was removed and the mixture was stirred for 30 min at room temperature. The solvent was then removed under reduced pressure and the resulting solid was dissolved in 50% diethyl ether in EtOAc (5 L), washed with saturated aqueous NH4Cl (800 mL×3), brine (800 mL), dried over Na2SO4, filtered, and evaporated to give 215 g (87% yield) of 1,4-dioxaspiro[4.5]decan-8-ol. GC-MS: 159 (M+1).

Workup

  1. customthe internal temperature <10° C.
  2. customThe ice bath was removed
  3. customThe solvent was then removed under reduced pressure
  4. dissolutionthe resulting solid was dissolved in 50% diethyl ether in EtOAc (5 L)
  5. washwashed with saturated aqueous NH4Cl (800 mL×3), brine (800 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-8381bc253a914e239885a6b6feb559e9
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

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