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

HRID 1193384Notes

Reaction equation

HRID 1193384 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 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,4-Dioxaspiro[4.5]decan-8-one (5.4 g, 34.571 ml, 1.0 eq.) was dissolved in MeOH (35 ml). NaBH4 (1.57 g, 41.485 mmol, 1.2 eq.) was added at 0° C. and the mixture was stirred for 1 hour at RT. After monitoring by TLC, the reaction mixture was concentrated and the residue was taken up in water (100 ml) and extracted with DCM (2×150 ml). The combined org. phases were washed with water (150 ml) and sat. NaCl solution (200 ml), dried over sodium sulfate, concentrated under reduced pressure and used in the next stage without being purified further. Yield: 90% (4.9 g, 31.012 mmol)

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with DCM (2×150 ml)
  3. washphases were washed with water (150 ml) and sat. NaCl solution (200 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customwithout being purified further

Sources & evidence

ORD record
ord-bcd4e1cd747749918da36b29f9f61d21
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…