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

HRID 555843Notes

Reaction equation

HRID 555843 reaction equation
[BH4-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1>CO>[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]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-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (4.84 g, 128 mmol) was added in 1 g portions over 30 min to a solution of 1,4-dioxaspiro[4.5]decan-8-one (20.0 g, 128 mmol) in MeOH (400 mL) at 0° C. The ice bath was removed and the mixture was stirred for another 30 min while keeping the temperature of the mixture around room room temperature. The solvent was then removed in vacuo and then the resulting solid was suspended in 1:1 Et2O/EtOAc (400 mL). The boron salts were dissolved by the addition of sat. aqueous ammonium chloride, and the resulting layers were separated. The organic layer was washed with saturated aqueous ammonium chloride (2×), brine (1×), dried over magnesium sulfate, filtered, and concentrated in vacuo to give 1,4-dioxaspiro[4.5]decan-8-ol.

Workup

  1. customThe ice bath was removed
  2. customaround room room temperature
  3. customThe solvent was then removed in vacuo
  4. dissolutionThe boron salts were dissolved by the addition of sat. aqueous ammonium chloride
  5. customthe resulting layers were separated
  6. washThe organic layer was washed with saturated aqueous ammonium chloride (2×), brine (1×)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fa0f2dddd654a39a323a607f25366be
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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