Sodium borohydride → 3,3-Diethyl-1,5-dioxaspiro[5.5]undecan-9-ol

HRID 342474

Reaction equation

HRID 342474 reaction equation
[BH4-].[Na+].[CH2:3]([C:5]1([CH2:17][CH3:18])[CH2:10][O:9][C:8]2([CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[O:7][CH2:6]1)[CH3:4]>C(O)C>[CH2:17]([C:5]1([CH2:3][CH3:4])[CH2:6][O:7][C:8]2([CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[O:9][CH2:10]1)[CH3:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 676976933,3-Diethyl-1,5-dioxaspiro[5.5]undecan-9-one

Product 1

HCID 153464673,3-Diethyl-1,5-dioxaspiro[5.5]undecan-9-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

820 mg (21.5 mmol) of sodium borohydride were added to a solution of 13 g (57.4 nmol) of 3,3-diethyl-1,5-dioxaspiro[5.5]undecan-9-one in 200 ml of ethanol and the mixture was stirred at room temperature for 1 hour. To complete the reaction, the mixture was heated at 40° C. for a further 15 hours. To destroy excess sodium borohydride, approximately 5 ml of acetone were added to the reaction solution and stirring was continued at 40° C. for a further 30 minutes. The reaction solution was subsequently concentrated in vacuo and the product taken up in ether and washed using ammonium chloride solution and water. The organic phase was dried carefully over magnesium sulfate and subsequently evaporated to dryness. This gave 11.8 g (90.0%) of the desired cyclohexanol. The crude product was further reacted without further purification.

Workup

  1. customthe reaction
  2. temperaturethe mixture was heated at 40° C. for a further 15 hours
  3. customTo destroy excess sodium borohydride, approximately 5 ml of acetone
  4. additionwere added to the reaction solution
  5. stirringstirring
  6. waitwas continued at 40° C. for a further 30 minutes
  7. concentrationThe reaction solution was subsequently concentrated in vacuo
  8. washwashed
  9. dry with materialThe organic phase was dried carefully over magnesium sulfate
  10. customsubsequently evaporated to dryness
  11. customThe crude product was further reacted without further purification

Sources & evidence

ORD record
ord-fd222acf8ba64ca886ef1a80a1c72554
Source dataset
uspto-grants-1999_01
Patent number
US05859009

Linked notes

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