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

HRID 1968960Notes

Reaction equation

HRID 1968960 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+]>C(O)C>[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-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,4-Dioxaspiro[4.5]decan-8-one (64 mmol, 10 g) was dissolved in ethanol (125 mL) and treated with NaBH4 (1.2 eq., 76.8 mmol, 2.9 g), at 0° C. portionwise and the mixture was stirred at room temperature for 1 hour. Reaction was quenched with NaOH (25 mL, 2N aqueous solution). The aqueous solution was extracted with dichloromethane (2×). The organics were combined, dried over Na2SO4, filtered and the solvent was evaporated to afford the title compound, 8.3 g, 82%, as a colourless oil.

Workup

  1. customReaction
  2. customwas quenched with NaOH (25 mL, 2N aqueous solution)
  3. extractionThe aqueous solution was extracted with dichloromethane (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-849d403e3dd94fd4b5d09d89312e387a
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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