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

HRID 1849801Notes

Reaction equation

HRID 1849801 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 54.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,4-dioxaspiro[4.5]decan-8-one (20.40 g, 130.60 mmol) in anhydrous methanol (200 mL) at 0° C., under nitrogen, was treated with sodium borohydride (2.50 g, 65.30 mmol), portion wise. The resulting mixture was stirred for 24 hours and concentrated in vacuo to dryness. The residue was diluted with ethyl acetate (300 mL), washed with 1 M hydrochloric acid (3×100 mL), brine (3×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound as a colorless oil (11.2 g, 51%): 1H NMR (300 MHz, CDCl3) δ 3.91-3.87 (m, 4H), 3.79-3.70 (m, 1H), 1.92 (br s, 1H), 1.89-1.71 (m, 4H), 1.67-1.47 (m, 4H); MS (ES+) m/z 140.9 (M-OH).

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. additionThe residue was diluted with ethyl acetate (300 mL)
  3. washwashed with 1 M hydrochloric acid (3×100 mL), brine (3×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-800b42a9c6564c2e88e561f732eb07db
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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