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

HRID 2070088Notes

Reaction equation

HRID 2070088 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 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,4-Dioxaspiro[4.5]decan-8-one (60 g, 384 mmol) was dissolved in methanol (600 mL) under Argon, then sodium borohydride (15.99 g, 423 mmol) was added portionwise (the addition was exothermic and a huge gas evolution was observed). The resulting mixture was stirred for 30 min. The reaction was quenched with water (200 mL) and stirred for 10 min. Solvent was removed under reduced pressure and the residue taken-up with DCM (600 mL) and water (300 mL). Phases were separated then the aqueous phase extracted with DCM (1×600 mL). Combined organic phases were dried on Na2SO4 and concentrated under vacuum to obtain title material (58 g; 95%) as colourless oil.

Workup

  1. additionthe addition
  2. customThe reaction was quenched with water (200 mL)
  3. stirringstirred for 10 min
  4. customSolvent was removed under reduced pressure
  5. customPhases were separated
  6. extractionthe aqueous phase extracted with DCM (1×600 mL)
  7. customCombined organic phases were dried on Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-915a69081fb24f4fa249d44b804656e6
Source dataset
uspto-grants-2012_10
Patent number
US08299257B2

Reaction notes

Loading…