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

HRID 1816329Notes

Reaction equation

HRID 1816329 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 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,4-dioxaspiro[4,5]decan-8-one (96.9 g) in methanol (1 l) was added portionwise sodium borohydride (46.9 g) under ice-cooling. After stirring for 3.5 hours under ice cooling, the reaction mixture was successively stirred for 3 hours at room temperature. Then the solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (1:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 1,4-dioxaspiro-[4,5]decan-8-ol (97.9 g).

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was successively stirred for 3 hours at room temperature
  3. customThen the solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (1:1)
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-483e94f7a17041cd889e8f66579e4bf3
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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